1-(4-amino-2-chlorophenyl)ethanone

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

Procedure: Iron (2.7 g), ammonium chloride (2.6 g) and water (8.1 ml) were added to a solution of 1-(2-chloro-4-nitro-phenyl)-ethanone ([CAS Reg. No. 67818-41-1], 960 mg) in ethanol (68 ml), which was made from 2-chloro-4-nitro-benzoyl chloride and malonic acid dimethyl ester according to a procedure from Dai et al.; J. Med. Chem. 2005, 48, 6066. The mixture was heated 1 h under reflux. DCM (35 ml) was added, stirred for 2 min and filtered over Celite. The residue was washed with DCM (50 ml). Water (100 ml) was added to the combined organic layers, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (837 mg) as light yellow oil, which was used in the next step without further purification. MS (m/e)=170.1 [M+H+]. The mixture was heated 1 h under reflux filtered over Celite The residue was washed with DCM (50 ml) Water (100 ml) was added to the combined organic layers extracted with DCM The combined organic layers were dried over Na2SO4 concentrated in vacuo

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

Procedure: Iron (2.7 g), ammonium chloride (2.6 g) and water (8.1 ml) were added to a solution of 1-(2-chloro-4-nitro-phenyl)-ethanone ([CAS Reg. No. 67818-41-1], 960 mg) in ethanol (68 ml), which was made from 2-chloro-4-nitro-benzoyl chloride and malonic acid dimethyl ester according to a procedure from Dai et al.; J. Med. Chem. 2005, 48, 6066. The mixture was heated 1 h under reflux. DCM (35 ml) was added, stirred for 2 min and filtered over Celite. The residue was washed with DCM (50 ml). Water (100 ml) was added to the combined organic layers, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (837 mg) as light yellow oil, which was used in the next step without further purification. MS (m/e)=170.1 [M+H+]. The mixture was heated 1 h under reflux filtered over Celite The residue was washed with DCM (50 ml) Water (100 ml) was added to the combined organic layers extracted with DCM The combined organic layers were dried over Na2SO4 concentrated in vacuo

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

Procedure: Iron (2.7 g), ammonium chloride (2.6 g) and water (8.1 ml) were added to a solution of 1-(2-chloro-4-nitro-phenyl)-ethanone ([CAS Reg. No. 67818-41-1], 960 mg) in ethanol (68 ml), which was made from 2-chloro-4-nitro-benzoyl chloride and malonic acid dimethyl ester according to a procedure from Dai et al.; J. Med. Chem. 2005, 48, 6066. The mixture was heated 1 h under reflux. DCM (35 ml) was added, stirred for 2 min and filtered over Celite. The residue was washed with DCM (50 ml). Water (100 ml) was added to the combined organic layers, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (837 mg) as light yellow oil, which was used in the next step without further purification. MS (m/e)=170.1 [M+H+]. The mixture was heated 1 h under reflux filtered over Celite The residue was washed with DCM (50 ml) Water (100 ml) was added to the combined organic layers extracted with DCM The combined organic layers were dried over Na2SO4 concentrated in vacuo

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

Procedure: Iron (2.7 g) and ammonium chloride (2.6 g) were added to a solution of 2′-chloro-4′-nitroacetophenone (CAS Reg. No. 67818-41-1, 960 mg) in ethanol (68 ml) and water (8.1 ml). The mixture was heated for 1 h under reflux. DCM (35 ml) was added and stirred for 2 min. The mixture was filtered over Celite. Water (100 ml) was added and extracted with DCM (200 ml, and 2×150 ml). The combined organic layers were dried over Na2SO4 and concentrated to give the title compound (837 mg) as light yellow oil. MS (m/e)=170.1 [M+H+]. The mixture was heated for 1 h under reflux The mixture was filtered over Celite Water (100 ml) was added extracted with DCM (200 ml, and 2×150 ml) The combined organic layers were dried over Na2SO4 concentrated

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

Procedure: Iron (2.7 g), ammonium chloride (2.6 g) and water (8.1 ml) were added to a solution of 1-(2-chloro-4-nitro-phenyl)-ethanone ([CAS Reg. No. 67818-41-1], 960 mg) in ethanol (68 ml), which was made from 2-chloro-4-nitro-benzoyl chloride and malonic acid dimethyl ester according to a procedure from Dai et al.; J. Med. Chem. 2005, 48, 6066. The mixture was heated 1 h under reflux. DCM (35 ml) was added, stirred for 2 min and filtered over Celite. The residue was washed with DCM (50 ml). Water (100 ml) was added to the combined organic layers, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (837 mg) as light yellow oil, which was used in the next step without further purification. MS (m/e)=170.1 [M+H+]. The mixture was heated 1 h under reflux filtered over Celite The residue was washed with DCM (50 ml) Water (100 ml) was added to the combined organic layers extracted with DCM The combined organic layers were dried over Na2SO4 concentrated in vacuo

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

Procedure: Iron (2.7 g), ammonium chloride (2.6 g) and water (8.1 ml) were added to a solution of 1-(2-chloro-4-nitro-phenyl)-ethanone ([CAS Reg. No. 67818-41-1], 960 mg) in ethanol (68 ml), which was made from 2-chloro-4-nitro-benzoyl chloride and malonic acid dimethyl ester according to a procedure from Dai et al.; J. Med. Chem. 2005, 48, 6066. The mixture was heated 1 h under reflux. DCM (35 ml) was added, stirred for 2 min and filtered over Celite. The residue was washed with DCM (50 ml). Water (100 ml) was added to the combined organic layers, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (837 mg) as light yellow oil, which was used in the next step without further purification. MS (m/e)=170.1 [M+H+]. The mixture was heated 1 h under reflux filtered over Celite The residue was washed with DCM (50 ml) Water (100 ml) was added to the combined organic layers extracted with DCM The combined organic layers were dried over Na2SO4 concentrated in vacuo

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

Procedure: Iron (2.7 g), ammonium chloride (2.6 g) and water (8.1 ml) were added to a solution of 1-(2-chloro-4-nitro-phenyl)-ethanone ([CAS Reg. No. 67818-41-1], 960 mg) in ethanol (68 ml), which was made from 2-chloro-4-nitro-benzoyl chloride and malonic acid dimethyl ester according to a procedure from Dai et al.; J. Med. Chem. 2005, 48, 6066. The mixture was heated 1 h under reflux. DCM (35 ml) was added, stirred for 2 min and filtered over Celite. The residue was washed with DCM (50 ml). Water (100 ml) was added to the combined organic layers, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (837 mg) as light yellow oil, which was used in the next step without further purification. MS (m/e)=170.1 [M+H+]. The mixture was heated 1 h under reflux filtered over Celite The residue was washed with DCM (50 ml) Water (100 ml) was added to the combined organic layers extracted with DCM The combined organic layers were dried over Na2SO4 concentrated in vacuo

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

Procedure: Iron (2.7 g) and ammonium chloride (2.6 g) were added to a solution of 2′-chloro-4′-nitroacetophenone (CAS Reg. No. 67818-41-1, 960 mg) in ethanol (68 ml) and water (8.1 ml). The mixture was heated for 1 h under reflux. DCM (35 ml) was added and stirred for 2 min. The mixture was filtered over Celite. Water (100 ml) was added and extracted with DCM (200 ml, and 2×150 ml). The combined organic layers were dried over Na2SO4 and concentrated to give the title compound (837 mg) as light yellow oil. MS (m/e)=170.1 [M+H+]. The mixture was heated for 1 h under reflux The mixture was filtered over Celite Water (100 ml) was added extracted with DCM (200 ml, and 2×150 ml) The combined organic layers were dried over Na2SO4 concentrated

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

Procedure: Iron (2.7 g), ammonium chloride (2.6 g) and water (8.1 ml) were added to a solution of 1-(2-chloro-4-nitro-phenyl)-ethanone ([CAS Reg. No. 67818-41-1], 960 mg) in ethanol (68 ml), which was made from 2-chloro-4-nitro-benzoyl chloride and malonic acid dimethyl ester according to a procedure from Dai et al.; J. Med. Chem. 2005, 48, 6066. The mixture was heated 1 h under reflux. DCM (35 ml) was added, stirred for 2 min and filtered over Celite. The residue was washed with DCM (50 ml). Water (100 ml) was added to the combined organic layers, and then extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the title compound (837 mg) as light yellow oil, which was used in the next step without further purification. MS (m/e)=170.1 [M+H+]. The mixture was heated 1 h under reflux filtered over Celite The residue was washed with DCM (50 ml) Water (100 ml) was added to the combined organic layers extracted with DCM The combined organic layers were dried over Na2SO4 concentrated in vacuo