Hydrazine → 4-(Aminomethyl)-3-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

4-(Bromomethyl)-3-fluorobenzonitrile (CAS 105942-09-4, 21 g) was dissolved in DMF (90 ml). Phthalimide potassium salt (19.64 g) was added and the mixture was stirred for 9 h at 130° C. After cooling to rt, the mixture was poured on ice. The solid was filtered off. Ethyl acetate and water were added and extracted with ethyl acetate. The organic phase was washed with water, dried, filtered and evaporated to give a light brown solid (14.1 g, 42% pure as judged by NMR). This solid was suspended in ethanol (50 ml). A solution of hydrazine in water (24%, 15 ml) was added and the mixture was refluxed for a total of 14 h. The mixture was filtered and the solvent was evaporated. The product was purified by chromatography (silica gel, CH2Cl2=>CH2Cl2/MeOH 4:1) to give 4-aminomethyl-3-fluoro-benzonitrile (0.63 g) as a brown oil.

Provenance & Evidence