Ammonia → HCID 58707283, compound

Participants

Reaction Steps

To a stirred solution of 1-(5-fluoro-2-methoxy-3-chlorophenyl)ethanone (1.9 g, 9.38 mmol), titanium(IV) isopropoxide (5.54 mL, 18.76 mmol) and ammonia in ethanol (23.5 mL) was stirred under nitrogen in a capped flask at ambient temperature for 6 h. Sodium borohydride (0.53 g, 14.07 mmol) was added and resulting mixture was stirred at room temperature for 3 h. The reaction was then quenched by pouring into ammonium hydroxide (40 mL), the resulting inorganic precipitate was filtered off, and washed with ethyl acetate (2×40 mL). the organic layer was separated and aqueous layer was extracted with ethyl acetate (2×40 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated to afford 1-(5-Fluoro-2-methoxy-3-chlorophenyl)ethanamine (1.7 g, 89%): 1H NMR (400 MHz, CDCl3): δ 6.78 (dd, 1H), 6.68 (dd, 1H), 4.25 (m, 1H), 3.82 (s, 3H), 1.42 (d, 3H).

Provenance & Evidence