2-(二甲氨基)乙腈

反应条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Hydroxylamine hydrochloride (1.24 g 17.8 mmol) was added to a solution of sodium (0.64 g, 26 mmol) in MeOH (100 mL). The reaction mixture was stirred at 25° C. for 15 min then dimethylaminoacetonitrile (1.5 g, 17.8 mmol) in MeOH (5 mL) was added and the reaction mixture stirred at 25° C. for a further 5 days. The solid was removed by filtration and the liquid concentrated under reduced pressure. The crude material was taken up in dry THF (100 mL) and sodium hydride (0.114 g, 60%, 2.86 mmol) was added and the reaction mixture was heated to 50° C. 1-Benzylindazole-3-carboxylic acid methyl ester (0.25 g, 0.938 mmol) was added and the reaction mixture was heated at reflux for 4 h. The THF was removed under reduced pressure and the residue partitioned between chloroform (100 mL) and H2O (100 mL). The chloroform layer was separated and the aqueous layer was further extracted with 2×100 mL of chloroform. The combined extracts were dried (MgSO4) and concentrated under reduced pressure. The crude compound was purified by flash chromatography using chloroform/MeOH (97.5:2.5) to afford the title compound (0.151 g, 48%) as a yellow solid. Mp 93–95° C. 1H NMR (300 MHz, CDCl3) ppm 2.40 (s, 6H), 3.77 (s, 2H), 5.68 (s, 2H), 7.19–7.37 (m, 8H), 8.27–8.30 (m, 2H). MS(FAB) m/z 334 [M+H]+. HRMS Calcd. for C19H20N5O: 334.1668. Found: 334.1655 [M+H]+. the reaction mixture stirred at 25° C. for a further 5 days The solid was removed by filtration the liquid concentrated under reduced pressure the reaction mixture was heated to 50° C the reaction mixture was heated at reflux for 4 h The THF was removed under reduced pressure the residue partitioned between chloroform (100 mL) and H2O (100 mL) The chloroform layer was separated the aqueous layer was further extracted with 2×100 mL of chloroform The combined extracts were dried (MgSO4) concentrated under reduced pressure The crude compound was purified by flash chromatography

反应条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Hydroxylamine hydrochloride (124 g 17.8 mmol) was added to a solution of sodium (0.64 g, 26 mmol) in MeOH (100 mL). The reaction mixture was stirred at 25° C. for 15 min then dimethylaminoacetonitrile (1.5 g, 17.8 mmol) in MeOH (5 mL) was added and the reaction mixture stirred at 25° C. for a further 5 days. The solid was removed by filtration and the liquid concentrated under reduced pressure. The crude material was taken up in dry THF (100 mL) and sodium hydride (0.114 g, 60%, 2.86 mmol) was added and the reaction mixture was heated to 50° C. 1-Benzylindazole-3-carboxylic acid methyl ester (0.25 g, 0.938 mmol) was added and the reaction mixture was heated at reflux for 4 h. The THF was removed under reduced pressure and the residue partitioned between chloroform (100 mL) and H2O (100 mL). The chloroform layer was separated and the aqueous layer was further extracted with 2×100 mL of chloroform. The combined extracts were dried (MgSO4) and concentrated under reduced pressure. The crude compound was purified by flash chromatography using chloroform/MeOH (97.5:2.5) to afford the title compound (0.151 g, 48%) as a yellow solid. Mp 93-95° C. 1H NMR (300 MHz, CDCl3) ppm 2.40 (s, 6H), 3.77 (s, 2H), 5.68 (s, 2H), 7.19-7.37 (m, 8H), 8.27-8.30 (m, 211). MS(FAB) m/z 334 [M+H]+. HRMS Calcd. for C19H20N5O: 334.1668. Found: 334.1655 [M+H]+. the reaction mixture stirred at 25° C. for a further 5 days The solid was removed by filtration the liquid concentrated under reduced pressure the reaction mixture was heated to 50° C the reaction mixture was heated at reflux for 4 h The THF was removed under reduced pressure the residue partitioned between chloroform (100 mL) and H2O (100 mL) The chloroform layer was separated the aqueous layer was further extracted with 2×100 mL of chloroform The combined extracts were dried (MgSO4) concentrated under reduced pressure The crude compound was purified by flash chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Dimethylamino acetonitrile (4.2 g, 0.05 mole) was dissolved in dry acetonitrile (50 ml) in a 100 ml RB flask provided with condenser, calcium chloride drying tube, and anti-bumping granules. Methyl p-toluene sulphonate (9.3 g, 0.05 mole) was added and the solution refluxed for 5 hours. The flask was cooled in ice, and the white solid crystalline solid filtered off, washed with ice-cold dry acetonitrile and then vacuum-dried to give 10.65 g of product, yield 78.8%: 'H NMR (σ, D2O) 2.4 (s, 3H, CH3 -Ar), 3.4 (s, 9H, (CH3)3N+), 7.4+7.7 (dd, 4H, ArH) ppm. provided with condenser, calcium chloride drying tube the solution refluxed for 5 hours The flask was cooled in ice the white solid crystalline solid filtered off washed with ice-cold dry acetonitrile vacuum-dried