Ammonia → HCID 58707318, compound

Participants

Reaction Steps

To a stirred solution of 1-(5-fluoro-2-methoxy-3-methylphenyl)ethanone (1.2 g, 6.59 mmol), titanium(IV) isopropoxide (3.89 mL, 13.17 mmol) and ammonia in ethanol (16.5 mL) was stirred under nitrogen in a capped flask at ambient temperature for 6 h. Sodium borohydride (0.37 g, 9.88 mmol) was added and resulting mixture was stirred at room temperature for 3 h. The reaction was then quenched by pouring into ammonium hydroxide (30 mL), the resulting inorganic precipitate was filtered off, and washed with ethyl acetate (2×25 mL). the organic layer was separated and aqueous layer was extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated to afford 1-(5-Fluoro-2-methoxy-3-methylphenyl)ethanamine (1.0 g, 82%): 1H NMR (400 MHz, CDCl3): δ 6.98 (dd, 1H), 6.78 (dd, 1H), 4.15 (m, 1H), 3.82 (s, 3H), 2.31 (s, 3H), 1.45 (d, 3H).

Provenance & Evidence