4-amino-2,5-dimethylbenzonitrile

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

実験手順: A solution of 4-amino-2,5-dimethylbenzonitrile (preparation 31) (111 mg, 0.76 mmol) in acetic acid (5 ml) was treated with a solution of sodium nitrite (53 mg, 0.76 mmol) in water (1 ml). The resultant mixture was stirred at room temperature for 10 mins then left to stand for 48 hrs. The solvent was removed by evaporation and the residue purified by chromatography (SiO2, eluting with 50:50 hexane: ethyl acetate) to give the desired product (25 mg, 21%). 1H NMR (CD3OD) δ 2.60 (s, 3H), 7.50 (s, 1H), 8.15 (s, 1H), 8.20 (s, 1H). LRMS m/z=158.1 (M+1)+. then left The solvent was removed by evaporation the residue purified by chromatography (SiO2, eluting with 50:50 hexane: ethyl acetate)

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

実験手順: 2,5-Dimethyl-4-nitrobenzonitrile (500 mg, 2.84 mmol; purchased from Salor) was dissolved in ethanol (20 ml), treated with 10% Pd on carbon catalyst (50 mg) and stirred under a hydrogen atmosphere (10 psi, room temperature, 3 hr). The catalyst was removed by filtration and the solvent evaporated to dryness. The resultant mixture was dissolved in CH2Cl2 and washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2. Solvent was evaporated from the organic layer to give the desired product (brown solid, 350 mg, 84%). 1H NMR (CD3OD) δ 2.10 (s, 3H), 2.30 (s, 3H), 6.60 (s, 1H), 7.20 (s, 1H). LRMS m/z=147.4 (M+1)+. Found C 72.12, H 6.86, N 18.53%; C9H10N2.0.2H2O requires C 72.16, H 7.00, N 18.70%. The catalyst was removed by filtration the solvent evaporated to dryness The resultant mixture was dissolved in CH2Cl2 washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2 Solvent was evaporated from the organic layer

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

実験手順: 2,5-Dimethyl-4-nitrobenzonitrile (500 mg, 2.84 mmol; purchased from Salor) was dissolved in ethanol (20 ml), treated with 10% Pd on carbon catalyst (50 mg) and stirred under a hydrogen atmosphere (10 psi, room temperature, 3 hr). The catalyst was removed by filtration and the solvent evaporated to dryness. The resultant mixture was dissolved in CH2Cl2 and washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2. Solvent was evaporated from the organic layer to give the desired product (brown solid, 350 mg, 84%). 1H NMR (CD3OD) δ 2.10 (s, 3H), 2.30 (s, 3H), 6.60 (s, 1H), 7.20 (s, 1H). LRMS m/z=147.4 (M+1)+. Found C 72.12, H 6.86, N 18.53%; C9H10N2.0.2H2O requires C 72.16, H 7.00, N 18.70%. The catalyst was removed by filtration the solvent evaporated to dryness The resultant mixture was dissolved in CH2Cl2 washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2 Solvent was evaporated from the organic layer

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

実験手順: A solution of 4-amino-2,5-dimethylbenzonitrile (preparation 31) (111 mg, 0.76 mmol) in acetic acid (5 ml) was treated with a solution of sodium nitrite (53 mg, 0.76 mmol) in water (1 ml). The resultant mixture was stirred at room temperature for 10 mins then left to stand for 48 hrs. The solvent was removed by evaporation and the residue purified by chromatography (SiO2, eluting with 50:50 hexane:ethyl acetate) to give the desired product (25 mg, 21%). 1H NMR (CD3OD) δ 2.60 (s, 3H), 7.50 (s, 1H), 8.15 (s, 1H), 8.20 (s, 1H). LRMS m/z=158.1 (M+1)+. then left The solvent was removed by evaporation the residue purified by chromatography (SiO2, eluting with 50:50 hexane:ethyl acetate)

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

実験手順: A solution of 4-amino-2,5-dimethylbenzonitrile (preparation 31) (111 mg, 0.76 mmol) in acetic acid (5 ml) was treated with a solution of sodium nitrite (53 mg, 0.76 mmol) in water (1 ml). The resultant mixture was stirred at room temperature for 10 mins then left to stand for 48 hrs. The solvent was removed by evaporation and the residue purified by chromatography (SiO2, eluting with 50:50 hexane:ethyl acetate) to give the desired product (25 mg, 21%). 1H NMR (CD3OD) δ 2.60 (s, 3H), 7.50 (s, 1H), 8.15 (s, 1H), 8.20 (s, 1H). LRMS m/z=158.1 (M+1)+. then left The solvent was removed by evaporation the residue purified by chromatography (SiO2, eluting with 50:50 hexane:ethyl acetate)

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

実験手順: 2,5-Dimethyl-4-nitrobenzonitrile (500 mg, 2.84 mmol; purchased from Salor) was dissolved in ethanol (20 ml), treated with 10% Pd on carbon catalyst (50 mg) and stirred under a hydrogen atmosphere (10 psi, room temperature, 3 hr). The catalyst was removed by filtration and the solvent evaporated to dryness. The resultant mixture was dissolved in CH2Cl2 and washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2. Solvent was evaporated from the organic layer to give the desired product (brown solid, 350 mg, 84%). 1H NMR (CD3OD) δ 2.10 (s, 3H), 2.30 (s, 3H), 6.60 (s, 1H), 7.20 (s, 1H). LRMS m/z=147.4 (M+1)+. Found C, 72.12, H, 6.86, N, 18.53%; C9H10N2.0.2H2O requires C, 72.16, H, 7.00, N, 18.70%. The catalyst was removed by filtration the solvent evaporated to dryness The resultant mixture was dissolved in CH2Cl2 washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2 Solvent was evaporated from the organic layer

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

実験手順: A solution of 4-amino-2,5-dimethylbenzonitrile (preparation 31) (111 mg, 0.76 mmol) in acetic acid (5 ml) was treated with a solution of sodium nitrite (53 mg, 0.76 mmol) in water (1 ml). The resultant mixture was stirred at room temperature for 10 mins then left to stand for 48 hrs. The solvent was removed by evaporation and the residue purified by chromatography (SiO2, eluting with 50:50 hexane:ethyl acetate) to give the desired product (25 mg, 21%). 1H NMR (CD3OD) δ 2.60 (s, 3H), 7.50 (s, 1H), 8.15 (s, 1H), 8.20 (s, 1H). LRMS m/z=158.1 (M+1)+. then left The solvent was removed by evaporation the residue purified by chromatography (SiO2, eluting with 50:50 hexane:ethyl acetate)

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

実験手順: A solution of 4-amino-2,5-dimethylbenzonitrile (preparation 31) (111 mg, 0.76 mmol) in acetic acid (5 ml) was treated with a solution of sodium nitrite (53 mg, 0.76 mmol) in water (1 ml). The resultant mixture was stirred at room temperature for 10 mins then left to stand for 48 hrs. The solvent was removed by evaporation and the residue purified by chromatography (SiO2, eluting with 50:50 hexane: ethyl acetate) to give the desired product (25 mg, 21%). 1H NMR (CD3OD) δ 2.60 (s, 3H), 7.50 (s, 1H), 8.15 (s, 1H), 8.20 (s, 1H). LRMS m/z=158.1 (M+1)+. then left The solvent was removed by evaporation the residue purified by chromatography (SiO2, eluting with 50:50 hexane: ethyl acetate)

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

実験手順: 2,5-Dimethyl-4-nitrobenzonitrile (500 mg, 2.84 mmol; purchased from Salor) was dissolved in ethanol (20 ml), treated with 10% Pd on carbon catalyst (50 mg) and stirred under a hydrogen atmosphere (10 psi, room temperature, 3 hr). The catalyst was removed by filtration and the solvent evaporated to dryness. The resultant mixture was dissolved in CH2Cl2 and washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2. Solvent was evaporated from the organic layer to give the desired product (brown solid, 350 mg, 84%). 1H NMR (CD3OD) δ 2.10 (s, 3H), 2.30 (s, 3H), 6.60 (s, 1H), 7.20 (s, 1H). LRMS m/z=147.4 (M+1)+. Found C 72.12, H 6.86, N 18.53%; C9H10N2.0.2H2O requires C 72.16, H 7.00, N 18.70%. The catalyst was removed by filtration the solvent evaporated to dryness The resultant mixture was dissolved in CH2Cl2 washed with HCl (2N, 4×15 ml), aqueous layer was treated with NaHCO3 then extracted repeatedly with CH2Cl2 Solvent was evaporated from the organic layer