Methanesulfonamide, N-(2-aminophenyl)-N-methyl-

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

Procedure: To a solution of N-methyl-N-(2-nitrophenyl)methanesulfonamide (900 mg, 3.91 mmol) in methanol (5 mL) was added palladium on carbon (10% by weight, 416 mg, 0.39 mmol). The solution was purged with hydrogen and then stirred for 4 hours under 1 atm of hydrogen. The crude reaction was filtered, concentrated and purified by chromatography to provide N-(2-aminophenyl)-N-methylmethanesulfonamide (540 mg, 60% yield). Product not characterized. The solution was purged with hydrogen The crude reaction was filtered concentrated purified by chromatography

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

Procedure: 50.2 g of N-methyl-N-(2-nitrophenyl)methanesulfonamide, prepared by the procedure of Example 5, is added to 220 ml of concentrated HCl and contacted with 183.3 g of SnCl2.2H2O. The mixture is heated on a steam bath for one hour. The reaction mixture is treated with enough 5-10% NaOH to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C. The crude reaction mixture is then extracted with CH2Cl2. The CH2Cl2 extracts are dried with MgSO4 and then filtered and concentrated on a rotary evaporator. The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step. The mixture is heated on a steam bath for one hour to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C The crude reaction mixture is then extracted with CH2Cl2 The CH2Cl2 extracts are dried with MgSO4 filtered concentrated on a rotary evaporator The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step

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

Procedure: 50.2 g of N-methyl-N-(2-nitrophenyl)methanesulfonamide, prepared by the procedure of Example 5, is added to 220 ml of concentrated HCl and contacted with 183.3 g of SnCl2.2H2O. The mixture is heated on a steam bath for one hour. The reaction mixture is treated with enough 5-10% NaOH to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C. The crude reaction mixture is then extracted with CH2Cl2. The CH2Cl2 extracts are dried with MgSO4 and then filtered and concentrated on a rotary evaporator. The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step. The mixture is heated on a steam bath for one hour to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C The crude reaction mixture is then extracted with CH2Cl2 The CH2Cl2 extracts are dried with MgSO4 filtered concentrated on a rotary evaporator The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step

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

Procedure: 50.2 g of N-methyl-N-(2-nitrophenyl)methanesulfonamide, prepared by the procedure of Example 5, is added to 220 ml of concentrated HCl and contacted with 183.3 g of SnCl2.2H2O. The mixture is heated on a steam bath for one hour. The reaction mixture is treated with enough 5-10% NaOH to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C. The crude reaction mixture is then extracted with CH2Cl2. The CH2Cl2 extracts are dried with MgSO4 and then filtered and concentrated on a rotary evaporator. The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step. The mixture is heated on a steam bath for one hour to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C The crude reaction mixture is then extracted with CH2Cl2 The CH2Cl2 extracts are dried with MgSO4 filtered concentrated on a rotary evaporator The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step

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

Procedure: 50.2 g of N-methyl-N-(2-nitrophenyl)methanesulfonamide, prepared by the procedure of Example 5, is added to 220 ml of concentrated HCl and contacted with 183.3 g of SnCl2.2H2O. The mixture is heated on a steam bath for one hour. The reaction mixture is treated with enough 5-10% NaOH to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C. The crude reaction mixture is then extracted with CH2Cl2. The CH2Cl2 extracts are dried with MgSO4 and then filtered and concentrated on a rotary evaporator. The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step. The mixture is heated on a steam bath for one hour to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C The crude reaction mixture is then extracted with CH2Cl2 The CH2Cl2 extracts are dried with MgSO4 filtered concentrated on a rotary evaporator The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step

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

Procedure: To a solution of N-methyl-N-(2-nitrophenyl)methanesulfonamide (900 mg, 3.91 mmol) in methanol (5 mL) was added palladium on carbon (10% by weight, 416 mg, 0.39 mmol). The solution was purged with hydrogen and then stirred for 4 hours under 1 atm of hydrogen. The crude reaction was filtered, concentrated and purified by chromatography to provide N-(2-aminophenyl)-N-methylmethanesulfonamide (540 mg, 60% yield). Product not characterized. The solution was purged with hydrogen The crude reaction was filtered concentrated purified by chromatography

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

Procedure: 50.2 g of N-methyl-N-(2-nitrophenyl)methanesulfonamide, prepared by the procedure of Example 5, is added to 220 ml of concentrated HCl and contacted with 183.3 g of SnCl2.2H2O. The mixture is heated on a steam bath for one hour. The reaction mixture is treated with enough 5-10% NaOH to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C. The crude reaction mixture is then extracted with CH2Cl2. The CH2Cl2 extracts are dried with MgSO4 and then filtered and concentrated on a rotary evaporator. The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step. The mixture is heated on a steam bath for one hour to raise the pH to 9 while maintaining the temperature of the mixture less than 25° C The crude reaction mixture is then extracted with CH2Cl2 The CH2Cl2 extracts are dried with MgSO4 filtered concentrated on a rotary evaporator The solid product obtained (38.1 g), m.p. 138°-139° was used without further purification in the next step