4-[(2,3-dichlorophenyl)methyl]aniline

Conditions: temp:250.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(2,3-Dichlorobenzyl)phenylamine (10.0 g, 39.7 mmol) obtained in Step 2 was dissolved in toluene (100 ml) and diethyl ethoxymethylenemalonate (8.8 ml, 43.7 mmol) was added. The mixture was heated under reflux for 3 hrs. The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue. The mixture was stirred with heating at 250° C. for 3 hrs. After allowing the mixture to cool, n-hexane was added to the reaction solution and the precipitate was collected by filtration, washed with chloroform and vacuum-dried to give an object product (10.1 g, yield 68%) as a pale-yellow solid. The mixture was heated under reflux for 3 hrs The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue to cool n-hexane was added to the reaction solution the precipitate was collected by filtration washed with chloroform vacuum-dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,2-Dichloro-3-(4-nitrobenzyl)benzene (25.0 g, 88.6 mmol) obtained in Step 1 was dissolved in acetic acid (400 ml) and zinc powder (70 g, 1.1 mol) was added by portions at 0° C. The mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through Celite and washed with ethanol. The filtrate was concentrated under reduced pressure and the solid precipitated during concentration was collected by filtration. The solid obtained by the filtration was washed with diethyl ether, and dissolved in ethyl acetate (500 ml) and water (500 ml). A 4N aqueous sodium hydroxide solution was added to neutralize the aqueous layer. The organic layer was separated, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure and the solid precipitated during the concentration was collected by filtration. The solid obtained by filtration was washed with n-hexane and vacuum-dried to give an object product (18.1 g, yield 81%) as a pale-brown solid. The reaction mixture was filtered through Celite washed with ethanol The filtrate was concentrated under reduced pressure the solid precipitated during concentration was collected by filtration The solid obtained by the filtration was washed with diethyl ether dissolved in ethyl acetate (500 ml) A 4N aqueous sodium hydroxide solution was added The organic layer was separated the aqueous layer was further extracted with ethyl acetate washed with water and saturated brine dried over sodium sulfate After the filtration the filtrate was concentrated under reduced pressure the solid precipitated during the concentration was collected by filtration The solid obtained by filtration was washed with n-hexane vacuum-dried

Conditions: temp:250.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(2,3-Dichlorobenzyl)phenylamine (10.0 g, 39.7 mmol) obtained in Step 2 was dissolved in toluene (100 ml), diethyl ethoxymethylenemalonate (8.8 ml, 43.7 mmol) was added, and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, diphenyl ether (100 ml) was added to the residue to allow dissolution, and the mixture was stirred with heating at 250° C. for 3 hr. After allowing to cool, n-hexane was added to the reaction mixture, The precipitated solid was collected by filtration, washed with chloroform, and vacuum dried to give the object product (10.1 g, yield 68%) as a pale-yellow solid. the mixture was heated under reflux for 3 hr The reaction mixture was concentrated under reduced pressure, diphenyl ether (100 ml) was added to the residue dissolution to cool n-hexane was added to the reaction mixture The precipitated solid was collected by filtration washed with chloroform, and vacuum dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,2-Dichloro-3-(4-nitrobenzyl)benzene (25.0 g, 88.6 mmol) obtained in Step 1 was dissolved in acetic acid (400 ml), zinc powder (70 g, 1.1 mol) was added by portions at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite and washed with ethanol. The filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrated solid was washed with diethyl ether, and dissolved in ethyl acetate (500 ml) and water (500 ml), 4N aqueous sodium hydroxide solution was added to neutralize the aqueous layer. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrated solid was washed with n-hexane and vacuum dried to give the object product (18.1 g, yield 81%) as a pale-brown solid. The reaction mixture was filtered through celite washed with ethanol The filtrate was concentrated under reduced pressure the precipitated solid was collected by filtration on the way The filtrated solid was washed with diethyl ether dissolved in ethyl acetate (500 ml) water (500 ml), 4N aqueous sodium hydroxide solution was added The organic layer was separated the aqueous layer was further extracted with ethyl acetate The organic layers were combined washed with water and saturated brine dried over sodium sulfate After filtration the filtrate was concentrated under reduced pressure the precipitated solid was collected by filtration on the way The filtrated solid was washed with n-hexane and vacuum dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,2-Dichloro-3-(4-nitrobenzyl)benzene (25.0 g, 88.6 mmol) obtained in Step 1 was dissolved in acetic acid (400 ml), zinc powder (70 g, 1.1 mol) was added by portions at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite and washed with ethanol. The filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrated solid was washed with diethyl ether, and dissolved in ethyl acetate (500 ml) and water (500 ml), 4N aqueous sodium hydroxide solution was added to neutralize the aqueous layer. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrated solid was washed with n-hexane and vacuum dried to give the object product (18.1 g, yield 81%) as a pale-brown solid. The reaction mixture was filtered through celite washed with ethanol The filtrate was concentrated under reduced pressure the precipitated solid was collected by filtration on the way The filtrated solid was washed with diethyl ether dissolved in ethyl acetate (500 ml) water (500 ml), 4N aqueous sodium hydroxide solution was added The organic layer was separated the aqueous layer was further extracted with ethyl acetate The organic layers were combined washed with water and saturated brine dried over sodium sulfate After filtration the filtrate was concentrated under reduced pressure the precipitated solid was collected by filtration on the way The filtrated solid was washed with n-hexane and vacuum dried

Conditions: temp:250.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(2,3-Dichlorobenzyl)phenylamine (10.0 g, 39.7 mmol) obtained in Step 2 was dissolved in toluene (100 ml) and diethyl ethoxymethylenemalonate (8.8 ml, 43.7 mmol) was added. The mixture was heated under reflux for 3 hrs. The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue. The mixture was stirred with heating at 250° C. for 3 hrs. After allowing the mixture to cool, n-hexane was added to the reaction solution and the precipitate was collected by filtration, washed with chloroform and vacuum-dried to give an object product (10.1 g, yield 68%) as a pale-yellow solid. The mixture was heated under reflux for 3 hrs The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue to cool n-hexane was added to the reaction solution the precipitate was collected by filtration washed with chloroform vacuum-dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,2-Dichloro-3-(4-nitrobenzyl)benzene (25.0 g, 88.6 mmol) obtained in Step 1 was dissolved in acetic acid (400 ml) and zinc powder (70 g, 1.1 mol) was added by portions at 0° C. The mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through Celite and washed with ethanol. The filtrate was concentrated under reduced pressure and the solid precipitated during concentration was collected by filtration. The solid obtained by the filtration was washed with diethyl ether, and dissolved in ethyl acetate (500 ml) and water (500 ml). A 4N aqueous sodium hydroxide solution was added to neutralize the aqueous layer. The organic layer was separated, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure and the solid precipitated during the concentration was collected by filtration. The solid obtained by filtration was washed with n-hexane and vacuum-dried to give an object product (18.1 g, yield 81%) as a pale-brown solid. The reaction mixture was filtered through Celite washed with ethanol The filtrate was concentrated under reduced pressure the solid precipitated during concentration was collected by filtration The solid obtained by the filtration was washed with diethyl ether dissolved in ethyl acetate (500 ml) A 4N aqueous sodium hydroxide solution was added The organic layer was separated the aqueous layer was further extracted with ethyl acetate washed with water and saturated brine dried over sodium sulfate After the filtration the filtrate was concentrated under reduced pressure the solid precipitated during the concentration was collected by filtration The solid obtained by filtration was washed with n-hexane vacuum-dried

Conditions: temp:250.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(2,3-Dichlorobenzyl)phenylamine (10.0 g, 39.7 mmol) obtained in Step 2 was dissolved in toluene (100 ml) and diethyl ethoxymethylenemalonate (8.8 ml, 43.7 mmol) was added. The mixture was heated under reflux for 3 hrs. The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue. The mixture was stirred with heating at 250° C. for 3 hrs. After allowing the mixture to cool, n-hexane was added to the reaction solution and the precipitate was collected by filtration, washed with chloroform and vacuum-dried to give an object product (10.1 g, yield 68%) as a pale-yellow solid. The mixture was heated under reflux for 3 hrs The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue to cool n-hexane was added to the reaction solution the precipitate was collected by filtration washed with chloroform vacuum-dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,2-Dichloro-3-(4-nitrobenzyl)benzene (25.0 g, 88.6 mmol) obtained in Step 1 was dissolved in acetic acid (400 ml) and zinc powder (70 g, 1.1 mol) was added by portions at 0° C. The mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through Celite and washed with ethanol. The filtrate was concentrated under reduced pressure and the solid precipitated during concentration was collected by filtration. The solid obtained by the filtration was washed with diethyl ether, and dissolved in ethyl acetate (500 ml) and water (500 ml). A 4N aqueous sodium hydroxide solution was added to neutralize the aqueous layer. The organic layer was separated, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over sodium sulfate. After the filtration, the filtrate was concentrated under reduced pressure and the solid precipitated during the concentration was collected by filtration. The solid obtained by filtration was washed with n-hexane and vacuum-dried to give an object product (18.1 g, yield 81%) as a pale-brown solid. The reaction mixture was filtered through Celite washed with ethanol The filtrate was concentrated under reduced pressure the solid precipitated during concentration was collected by filtration The solid obtained by the filtration was washed with diethyl ether dissolved in ethyl acetate (500 ml) A 4N aqueous sodium hydroxide solution was added The organic layer was separated the aqueous layer was further extracted with ethyl acetate washed with water and saturated brine dried over sodium sulfate After the filtration the filtrate was concentrated under reduced pressure the solid precipitated during the concentration was collected by filtration The solid obtained by filtration was washed with n-hexane vacuum-dried

Conditions: temp:250.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(2,3-Dichlorobenzyl)phenylamine (10.0 g, 39.7 mmol) obtained in Step 2 was dissolved in toluene (100 ml), diethyl ethoxymethylenemalonate (8.8 ml, 43.7 mmol) was added, and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, diphenyl ether (100 ml) was added to the residue to allow dissolution, and the mixture was stirred with heating at 250° C. for 3 hr. After allowing to cool, n-hexane was added to the reaction mixture, The precipitated solid was collected by filtration, washed with chloroform, and vacuum dried to give the object product (10.1 g, yield 68%) as a pale-yellow solid. the mixture was heated under reflux for 3 hr The reaction mixture was concentrated under reduced pressure, diphenyl ether (100 ml) was added to the residue dissolution to cool n-hexane was added to the reaction mixture The precipitated solid was collected by filtration washed with chloroform, and vacuum dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,2-Dichloro-3-(4-nitrobenzyl)benzene (25.0 g, 88.6 mmol) obtained in Step 1 was dissolved in acetic acid (400 ml), zinc powder (70 g, 1.1 mol) was added by portions at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite and washed with ethanol. The filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrated solid was washed with diethyl ether, and dissolved in ethyl acetate (500 ml) and water (500 ml), 4N aqueous sodium hydroxide solution was added to neutralize the aqueous layer. The organic layer was separated and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the precipitated solid was collected by filtration on the way. The filtrated solid was washed with n-hexane and vacuum dried to give the object product (18.1 g, yield 81%) as a pale-brown solid. The reaction mixture was filtered through celite washed with ethanol The filtrate was concentrated under reduced pressure the precipitated solid was collected by filtration on the way The filtrated solid was washed with diethyl ether dissolved in ethyl acetate (500 ml) water (500 ml), 4N aqueous sodium hydroxide solution was added The organic layer was separated the aqueous layer was further extracted with ethyl acetate The organic layers were combined washed with water and saturated brine dried over sodium sulfate After filtration the filtrate was concentrated under reduced pressure the precipitated solid was collected by filtration on the way The filtrated solid was washed with n-hexane and vacuum dried

Conditions: temp:250.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-(2,3-Dichlorobenzyl)phenylamine (10.0 g, 39.7 mmol) obtained in Step 2 was dissolved in toluene (100 ml) and diethyl ethoxymethylenemalonate (8.8 ml, 43.7 mmol) was added. The mixture was heated under reflux for 3 hrs. The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue. The mixture was stirred with heating at 250° C. for 3 hrs. After allowing the mixture to cool, n-hexane was added to the reaction solution and the precipitate was collected by filtration, washed with chloroform and vacuum-dried to give an object product (10.1 g, yield 68%) as a pale-yellow solid. The mixture was heated under reflux for 3 hrs The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue to cool n-hexane was added to the reaction solution the precipitate was collected by filtration washed with chloroform vacuum-dried