methyl 2-amino-3,5-dichlorobenzoate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 20 parts of a 30 percent strength by weight solution of sodium methylate in methanol are added to 21.6 parts of 5,7-dichloroisatin in 300 parts of methanol at -10° C., resulting in a dark violet suspension of a bulky precipitate. 7 parts of 50 percent strength by weight hydrogen peroxide solution are then added at -3° C. and thereafter the mixture is stirred for one hour at room temperature. The solution is concentrated and the crystalline residue is mixed with water and filtered off. 17.6 parts (80% of theory) of methyl 3,5-dichloroanthranilate, of melting point 62°-63° C., are obtained. resulting in a dark violet suspension of a bulky precipitate The solution is concentrated the crystalline residue is mixed with water filtered off

Conditions: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL round-bottom flask, 0.1 mol of 2-amino-3,5-dichlorobenzoic acid methyl ester having a structure as shown in VIII-1, 100 mL of methanol, and 0.4 mol of tert-butylamine were added, heated to 64° C. and reacted for 5 hours, after treatment 23.5 grams of N-tert-butyl-2-amino-3,5-dichlorobenzamide having a structural formula of III-1 was obtained, and the yield was 90.4%; were added reacted for 5 hours

Conditions: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL round-bottom flask, 0.2 mol of 2-amino-3,5-dichlorobenzoic acid having a structural formula of IV-4, 300 mL of methanol, and 5 mL of concentrated sulfuric acid were added, heated to 64° C. and reacted for 12 hours (into which 3 mL of concentrated sulfuric acid was added twice), after cooling most of the solvent was removed under reduced pressure, and 300 mL of water was added, the pH was adjusted to 9-10 with a saturated sodium hydroxide solution, extracted with 200 mL of ethyl acetate, washed with water for one time, dried over anhydrous sodium sulfate, filtered and the solvent was remove to obtain a crude product, 34.6 grams of 2-amino-3,5-dichlorobenzoic acid methyl ester having a structure as shown by VIII-1 was obtained by column chromatography, and the yield was 78.6%; was added twice), after cooling most of the solvent was removed under reduced pressure, and 300 mL of water was added extracted with 200 mL of ethyl acetate washed with water for one time dried over anhydrous sodium sulfate filtered the solvent was remove

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9 g (40.9 mmol) of methyl 3,5-dichloro-2-aminobenzoate and 6.3 g (81.8 mmol) of 2-(aminooxy)ethanol are initially charged in 90 ml of methanol, and 22.1 g (122.7 mmol) of sodium methoxide as a 30% strength solution in methanol are added dropwise at 20° C. The mixture is stirred at 50° C. overnight. The mixture is cooled and poured onto 400 ml of water, and the pH is adjusted to 3 using 1 N hydrochloric acid. The mixture is extracted 3 times with in each case 150 ml of ethyl acetate and the extracts are dried with sodium sulphate and concentrated using a rotary evaporator. The mixture is cooled The mixture is extracted 3 times with in each case 150 ml of ethyl acetate the extracts are dried with sodium sulphate concentrated a rotary evaporator

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9 g (40.9 mmol) of methyl 3,5-dichloro-2-aminobenzoate and 6.3 g (81.8 mmol) of 2-(aminooxy)ethanol are initially charged in 90 ml of methanol, and 22.1 g (122.7 mmol) of sodium methoxide as a 30% strength solution in methanol are added dropwise at 20° C. The mixture is stirred at 50° C. overnight. The mixture is cooled and poured onto 400 ml of water, and the pH is adjusted to 3 using 1 N hydrochloric acid. The mixture is extracted 3 times with in each case 150 ml of ethyl acetate and the extracts are dried with sodium sulphate and concentrated using a rotary evaporator. The mixture is cooled The mixture is extracted 3 times with in each case 150 ml of ethyl acetate the extracts are dried with sodium sulphate concentrated a rotary evaporator

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9 g (40.9 mmol) of methyl 3,5-dichloro-2-aminobenzoate and 6.3 g (81.8 mmol) of 2-(aminooxy)ethanol are initially charged in 90 ml of methanol, and 22.1 g (122.7 mmol) of sodium methoxide as a 30% strength solution in methanol are added dropwise at 20° C. The mixture is stirred at 50° C. overnight. The mixture is cooled and poured onto 400 ml of water, and the pH is adjusted to 3 using 1 N hydrochloric acid. The mixture is extracted 3 times with in each case 150 ml of ethyl acetate and the extracts are dried with sodium sulphate and concentrated using a rotary evaporator. The mixture is cooled The mixture is extracted 3 times with in each case 150 ml of ethyl acetate the extracts are dried with sodium sulphate concentrated a rotary evaporator

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9 g (40.9 mmol) of methyl 3,5-dichloro-2-aminobenzoate and 6.3 g (81.8 mmol) of 2-(aminooxy)ethanol are initially charged in 90 ml of methanol, and 22.1 g (122.7 mmol) of sodium methoxide as a 30% strength solution in methanol are added dropwise at 20° C. The mixture is stirred at 50° C. overnight. The mixture is cooled and poured onto 400 ml of water, and the pH is adjusted to 3 using 1 N hydrochloric acid. The mixture is extracted 3 times with in each case 150 ml of ethyl acetate and the extracts are dried with sodium sulphate and concentrated using a rotary evaporator. The mixture is cooled The mixture is extracted 3 times with in each case 150 ml of ethyl acetate the extracts are dried with sodium sulphate concentrated a rotary evaporator

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 20 parts of a 30 percent strength by weight solution of sodium methylate in methanol are added to 21.6 parts of 5,7-dichloroisatin in 300 parts of methanol at -10° C., resulting in a dark violet suspension of a bulky precipitate. 7 parts of 50 percent strength by weight hydrogen peroxide solution are then added at -3° C. and thereafter the mixture is stirred for one hour at room temperature. The solution is concentrated and the crystalline residue is mixed with water and filtered off. 17.6 parts (80% of theory) of methyl 3,5-dichloroanthranilate, of melting point 62°-63° C., are obtained. resulting in a dark violet suspension of a bulky precipitate The solution is concentrated the crystalline residue is mixed with water filtered off

Conditions: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL round-bottom flask, 0.1 mol of 2-amino-3,5-dichlorobenzoic acid methyl ester having a structure as shown in VIII-1, 100 mL of methanol, and 0.4 mol of tert-butylamine were added, heated to 64° C. and reacted for 5 hours, after treatment 23.5 grams of N-tert-butyl-2-amino-3,5-dichlorobenzamide having a structural formula of III-1 was obtained, and the yield was 90.4%; were added reacted for 5 hours

Conditions: temp:64.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL round-bottom flask, 0.2 mol of 2-amino-3,5-dichlorobenzoic acid having a structural formula of IV-4, 300 mL of methanol, and 5 mL of concentrated sulfuric acid were added, heated to 64° C. and reacted for 12 hours (into which 3 mL of concentrated sulfuric acid was added twice), after cooling most of the solvent was removed under reduced pressure, and 300 mL of water was added, the pH was adjusted to 9-10 with a saturated sodium hydroxide solution, extracted with 200 mL of ethyl acetate, washed with water for one time, dried over anhydrous sodium sulfate, filtered and the solvent was remove to obtain a crude product, 34.6 grams of 2-amino-3,5-dichlorobenzoic acid methyl ester having a structure as shown by VIII-1 was obtained by column chromatography, and the yield was 78.6%; was added twice), after cooling most of the solvent was removed under reduced pressure, and 300 mL of water was added extracted with 200 mL of ethyl acetate washed with water for one time dried over anhydrous sodium sulfate filtered the solvent was remove