Diisopropylethylamine → N-cyanomethyl-4-fluoro-2-hydroxy-benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of 4-fluorosalicylic acid chloride (Example 1, 10 g, 57.3 mmol) in dichloromethane (114 mL) was treated with N,N-diisopropylethyl amine (25 mL, 143 mmol) and acetonitrile hydrochloride (7.95 g, 85.9 mmol). After stirring at 35° C. for 24 h, the solution was concentrated under reduced pressure, diluted with ethyl acetate, and washed successively with 2 N HCl and saturated aq NaCl. The resulting solution was dried over MgSO4, filtered and concentrated. The resulting solid was suspended in dichloromethane, filtered and rinsed with heptane to give N-cyanomethyl-4-fluoro-2-hydroxy-benzamide (7.20 g, 65%): 1H NMR (DMSO-d6 300 MHz) δ 12.16 (br s, 1H), 9.17 (t, J=5.3 Hz, 1H), 7.88 (dd, J1=8.7 Hz, J2=6.3 Hz, 1H), 6.81-6.73 (m, 2H), 4.32 (d, J=5.7 Hz, 2H).

Provenance & Evidence