Dimethylformamide → Benzyl 6-amino-3-cyano-2-methylbenzoate

Participants

Reaction Steps

A mixture of Example 108A (2 g, 4.8 mmol), zinc cyanide (335 mg, 2.9 mmol), and DMF (48 mL) was degassed with argon for 30 minutes, treated with Pd(PPh3)4 (330 mg, 0.28 mmol), heated to reflux for 1.5 hours, cooled, and filtered. The filtrate was concentrated and purified using a Biotage 40 gram silica gel cartridge to provide the desired product. MS (ESI(−)) m/e 265 (M−H)−; (DCI) m/e 267 (M+H)+, 284 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 7.45 (m, 6H), 6.66 (d, 1H), 6.57 (s, 2H), 5.34 (s, 2H), 3.27 (s, 3H).

Provenance & Evidence