Ammonia → HCID 66705891, compound

Participants

Reaction Steps

To a stirred solution of 3-fluoro-2-methyl-benzaldehyde (5.0 g) in methanol (20 ml) were added sequentially ammonia solution (40.5 ml, 7 M solution in methanol) and tetraisopropyl orthotitanate (12.6 ml) and the resulting mixture was stirred at r.t. for 1 h. Trimethylsilylcyanide (4.69 ml) was then added dropwise and stirring continued at r.t. overnight. The reaction mixture was poured onto ice-water (400 ml) and the mixture was then extracted twice with ethyl acetate. The combined organic phases were washed with brine and then dried over sodium sulphate and concentrated in vacuo to afford (RS)-amino-(3-fluoro-2-methyl-phenyl)-acetonitrile (5.90 g, quant.) as an orange solid. 1H NMR δ (CDCl3, 300 MHz): 7.39 (1H, d, J=7.3 Hz), 7.31 (1H, m), 7.17 (1H, dd, J=9.6 & 9.6 Hz), 5.16 (1H, t, J=7.8 Hz), 5.16 (1H, d, J=7.8 Hz), 2.26 (1H, d, J=2.1 Hz).

Provenance & Evidence