2-amino-2-(2-methoxyphenyl)acetonitrile

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 50.0 g (1.0 mol) of sodium cyanide, 53.5 g (1.0 mol) of ammonium chloride, and 60 mL of concentrated ammonium hydroxide in 400 mL of water was added 125 g (0.92 mol) of o-anisaldehyde in 400 aromatic C-C); of dry methanol. After the mixture was stirred for 3 h at 23° C., the methanol was removed under reduced pressure, and the residual solution containing the crude product was diluted with 500 mL of water and extracted with methylene chloride (2×400 mL), dried over sodium sulfate, and filtered; the solvent was subsequently removed under vacuum to give an orange oil. By means of column chromatography on silica gel using ethyl acetate as the eluent, the o-amino nitrile compound (A) was separated from the starting material and the side products; IR (neat) 2240 (w, --C≡N), 1600, 1500 cm1 (s, aromatic C=C); NMR (CDCL3) 1.03 (2 H, s, NH2), 3.90 (3 H, s, OCH3), 5.05 (1 H, s, CH), 7.15 (4 H m, ArH). The α-amino nitrile (yellow oil) was unstable as a free base; therefore it was either used immediately for the next reaction or converted to the tartarate salt. the methanol was removed under reduced pressure the residual solution containing the crude product was diluted with 500 mL of water extracted with methylene chloride (2×400 mL) dried over sodium sulfate filtered the solvent was subsequently removed under vacuum to give an orange oil the o-amino nitrile compound (A) was separated from the starting material therefore it was either used immediately for the next reaction

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 50.0 g (1.0 mol) of sodium cyanide, 53.5 g (1.0 mol) of ammonium chloride, and 60 mL of concentrated ammonium hydroxide in 400 mL of water was added 125 g (0.92 mol) of o-anisaldehyde in 400 aromatic C-C); of dry methanol. After the mixture was stirred for 3 h at 23° C., the methanol was removed under reduced pressure, and the residual solution containing the crude product was diluted with 500 mL of water and extracted with methylene chloride (2×400 mL), dried over sodium sulfate, and filtered; the solvent was subsequently removed under vacuum to give an orange oil. By means of column chromatography on silica gel using ethyl acetate as the eluent, the o-amino nitrile compound (A) was separated from the starting material and the side products; IR (neat) 2240 (w, --C≡N), 1600, 1500 cm1 (s, aromatic C=C); NMR (CDCL3) 1.03 (2 H, s, NH2), 3.90 (3 H, s, OCH3), 5.05 (1 H, s, CH), 7.15 (4 H m, ArH). The α-amino nitrile (yellow oil) was unstable as a free base; therefore it was either used immediately for the next reaction or converted to the tartarate salt. the methanol was removed under reduced pressure the residual solution containing the crude product was diluted with 500 mL of water extracted with methylene chloride (2×400 mL) dried over sodium sulfate filtered the solvent was subsequently removed under vacuum to give an orange oil the o-amino nitrile compound (A) was separated from the starting material therefore it was either used immediately for the next reaction

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 50.0 g (1.0 mol) of sodium cyanide, 53.5 g (1.0 mol) of ammonium chloride, and 60 mL of concentrated ammonium hydroxide in 400 mL of water was added 125 g (0.92 mol) of o-anisaldehyde in 400 aromatic C-C); of dry methanol. After the mixture was stirred for 3 h at 23° C., the methanol was removed under reduced pressure, and the residual solution containing the crude product was diluted with 500 mL of water and extracted with methylene chloride (2×400 mL), dried over sodium sulfate, and filtered; the solvent was subsequently removed under vacuum to give an orange oil. By means of column chromatography on silica gel using ethyl acetate as the eluent, the o-amino nitrile compound (A) was separated from the starting material and the side products; IR (neat) 2240 (w, --C≡N), 1600, 1500 cm1 (s, aromatic C=C); NMR (CDCL3) 1.03 (2 H, s, NH2), 3.90 (3 H, s, OCH3), 5.05 (1 H, s, CH), 7.15 (4 H m, ArH). The α-amino nitrile (yellow oil) was unstable as a free base; therefore it was either used immediately for the next reaction or converted to the tartarate salt. the methanol was removed under reduced pressure the residual solution containing the crude product was diluted with 500 mL of water extracted with methylene chloride (2×400 mL) dried over sodium sulfate filtered the solvent was subsequently removed under vacuum to give an orange oil the o-amino nitrile compound (A) was separated from the starting material therefore it was either used immediately for the next reaction