Ammonia → 2-Amino-2-(4-iodophenyl)acetonitrile

Participants

Reaction Steps

To a stirred solution of 4-iodo-benzaldehyde (7.10 g) in methanol (25 ml) were added sequentially ammonia solution (35 ml, 7 M solution in methanol) and tetraisopropyl orthotitanate (10.9 ml) and the resulting mixture was stirred at r.t. for 2 h. Trimethylsilylcyanide (3.84 ml) was then added dropwise and stirring continued at r.t. for 22 hours. The reaction mixture was poured onto ice-water (100 ml) and after stirring the resulting mixture was filtered through celite, washing with ethyl acetate. The filtrate was concentrated in vacuo and the residue was taken up in ethyl acetate and washed sequentially with distilled water and with saturated brine. The organic phase was then dried over sodium sulphate and concentrated in vacuo to afford (RS)-amino-(4-iodo-phenyl)-acetonitrile (6.41 g, 81%) as a yellow solid. 1H NMR δ (CDCl3, 300 MHz): 7.76 (2H, d, J=7.8 Hz), 7.30 (2H, d, J=7.8 Hz), 4.87 (1H, brs), 1.94 (2H, brs).

Provenance & Evidence