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

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).

1. stirringstirring
2. waitcontinued at r.t. for 22 hours
3. additionThe reaction mixture was poured onto ice-water (100 ml)
4. stirringafter stirring the resulting mixture
5. filtrationwas filtered through celite
6. washwashing with ethyl acetate
7. concentrationThe filtrate was concentrated in vacuo
8. washwashed sequentially with distilled water and with saturated brine
9. dry with materialThe organic phase was then dried over sodium sulphate
10. concentrationconcentrated in vacuo

ORD record

ord-9c2bd845507f40ad9de2c6cba5082e1a

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354441B2