Methylamine → HCID 66967533, compound

Reaction equation

[CH3:1][NH2:2].[CH2:3]([O:5][C:6]1[C:13]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=O)[CH3:4].[BH4-].[Na+]>CO>[CH2:3]([O:5][C:6]1[C:13]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][CH2:1][NH2:2])[CH3:4]

Participants

Procedure

A solution of methylamine (20 mL of a 2.0 M solution if MeOH, 40 mmol) was added to 2-ethoxy-3-trifluoromethoxybenzaldehyde (1.17 g, 4.95 mmol) under N2 and the solution was stirred for 18 h. The solution was concentrated under reduced pressure. The resulting clear oil was dissolved in EtOH (20 mL) and treated with NaBH4 (0.187 g, 4.95 mmol). After stirring for 5.5 h, the reaction mixture was concentrated under reduced pressure, then dissolved in 1 N NaOH (20 mL) and extracted with Et2O (3×50 mL). The combined organics were collected, washed with brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (0.72 g, 58%) as a clear oil: 1H NMR (500 MHz, DMSO-d6) δ 7.40 (dd, J=7.7, 1.55 Hz, 1H), 7.25 (d, J=9.5 Hz, 1H), 7.16 (t, J=7.7 Hz, 1H), 3.97 (t, J=7.0 Hz, 2H), 3.68 (s, 2H), 2.28 (s, 3H), 2.02 (br s, 1H), 1.35-1.30 (m, 3H).