2-(3-amino-2-methylphenyl)acetonitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (3-Amino-2-methyl-phenyl)-acetonitrile (11.1 g) was dissolved in 80 ml of pyridine. The solution was cooled in an ice bath and 11.3 g of methanesulfonyl chloride was added. The reaction mixture was removed from the ice bath and stirred at room temperature for 30 minutes; 10 ml of water was added, and the mixture was stirred for 30 minutes, poured into ethyl acetate (EtOAc), washed with cold hydrochloric acid, washed with water, dried, and evaporated to give 16.1 g of N-(3-cyanomethyl-2-methyl-phenyl)-methanesulfonamide as a light yellow solid. ##STR120## The solution was cooled in an ice bath The reaction mixture was removed from the ice bath 10 ml of water was added the mixture was stirred for 30 minutes poured into ethyl acetate (EtOAc) washed with cold hydrochloric acid washed with water dried evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (2-Methyl-3-nitro-phenyl)-acetonitrile (16.6 g ) was dissolved in 400 ml of ethyl acetate and 0.83 g of 10% palladium on carbon (Degussa type) was added; and the reaction mixture was placed under 50 lb/in2 of hydrogen on the Parr shaker for 4 hr. The catalyst was filtered off; the solvent was evaporated; and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3), yielding 11.1 g of (3-amino-2-methyl-phenyl)-acetonitrile as a white solid. ##STR119## for 4 hr The catalyst was filtered off the solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (2-Methyl-3-nitro-phenyl)-acetonitrile (16.6 g ) was dissolved in 400 ml of ethyl acetate and 0.83 g of 10% palladium on carbon (Degussa type) was added; and the reaction mixture was placed under 50 lb/in2 of hydrogen on the Parr shaker for 4 hr. The catalyst was filtered off; the solvent was evaporated; and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3), yielding 11.1 g of (3-amino-2-methyl-phenyl)-acetonitrile as a white solid. ##STR119## for 4 hr The catalyst was filtered off the solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (3-Amino-2-methyl-phenyl)-acetonitrile (11.1 g) was dissolved in 80 ml of pyridine. The solution was cooled in an ice bath and 11.3g of methanesulfonyl chloride was added. The reaction mixture was removed from the ice bath and stirred at room temperature for 30 minutes; 10 ml of water was added, and the mixture was stirred for 30 minutes, poured into ethyl acetate (EtOAc), washed with cold hydrochloric acid, washed with water, dried, and evaporated to give 16.1 g of N-(3-cyanomethyl-2-methyl-phenyl)-methanesulfonamide as a light yellow solid. ##STR105## The solution was cooled in an ice bath The reaction mixture was removed from the ice bath 10 ml of water was added the mixture was stirred for 30 minutes poured into ethyl acetate (EtOAc) washed with cold hydrochloric acid washed with water dried evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (2-Methyl-3-nitro-phenyl)-acetonitrile (16.6g ) was dissolved in 400 ml of ethyl acetate and 0.83g of 10% palladium on carbon (Degussa type) was added; and the reaction mixture was placed under 50 lb/in2 of hydrogen on the Parr shaker for 4 hr. The catalyst was filtered off; the solvent was evaporated; and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3), yielding 11.1 g of (3-amino-2-methyl-phenyl)-acetonitrile as a white solid. ##STR104## for 4 hr The catalyst was filtered off the solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (2-Methyl-3-nitro-phenyl)-acetonitrile (16.6g ) was dissolved in 400 ml of ethyl acetate and 0.83g of 10% palladium on carbon (Degussa type) was added; and the reaction mixture was placed under 50 lb/in2 of hydrogen on the Parr shaker for 4 hr. The catalyst was filtered off; the solvent was evaporated; and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3), yielding 11.1 g of (3-amino-2-methyl-phenyl)-acetonitrile as a white solid. ##STR104## for 4 hr The catalyst was filtered off the solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with ethyl acetate:hexane (2:3)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2-Methyl-3-nitrophenyl)acetonitrile (Askam, V. et al. J. Chem. Soc. C (1969)1935–1936;) was hydrogenated over 5% palladium-charcoal 50 mg in EtOAc/EtOH 1:1 (14 ml) for three hours. The mixture was filtered through celite, and the filtrate was concentrated to give the title compound 77 mg (77%) as a white powder. The mixture was filtered through celite the filtrate was concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: (3-Amino-2-methyl-phenyl)-acetonitrile (11.1 g) was dissolved in 80 ml of pyridine. The solution was cooled in an ice bath and 11.3 g of methanesulfonyl chloride was added. The reaction mixture was removed from the ice bath and stirred at room temperature for 30 minutes; 10 ml of water was added, and the mixture was stirred for 30 minutes, poured into ethyl acetate (EtOAc), washed with cold hydrochloric acid, washed with water, dried, and evaporated to give 16.1 g of N-(3-cyanomethyl-2-methyl-phenyl)-methanesulfonamide as a light yellow solid. ##STR120## The solution was cooled in an ice bath The reaction mixture was removed from the ice bath 10 ml of water was added the mixture was stirred for 30 minutes poured into ethyl acetate (EtOAc) washed with cold hydrochloric acid washed with water dried evaporated