Dimethylamine, hydrochloride → HCID 59405027、化合物

反応式

[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([CH3:9])=[N:7][CH:8]=1)#[CH:2].Cl.[CH3:14][NH:15][CH3:16].C([BH3-])#N.[Na+]>CCO>[CH3:14][N:15]([CH3:16])[CH2:2][CH2:1][C:3]1[CH:8]=[N:7][C:6]([CH3:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

参加物

実験手順

To a solution of 5-ethynyl-2-methyl-3-nitropyridine (930 mg, 5.74 mmol) in EtOH (7 mL) were added dimethylamine hydrochloride (2.34 g, 28.7 mmol) and sodium cyanoborohydride (0.721 g, 11.5 mmol). The reaction mixture was allowed to stir at reflux for 24 h, concentrated, and treated with 4N NaOH (10 mL). The solution was extracted with DCM (2×200 mL). The organic solutions were combined, washed with brine (200 mL), dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N,N-dimethyl-2-(6-methyl-5-nitropyridin-3-yl)ethanamine (489 mg, 41%). LCMS (AA): Rt=1.35 min, m/z 210 (M+H).