Ammonia → HCID 66705891, compound

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).

1. stirringstirring
2. waitcontinued at r.t. overnight
3. additionThe reaction mixture was poured onto ice-water (400 ml)
4. extractionthe mixture was then extracted twice with ethyl acetate
5. washThe combined organic phases were washed with brine
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated in vacuo

ORD record

ord-03667d3595dc44628a671737da17855e

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09132136B2