Sodium cyanoborohydride → 1-(2-Fluorophenyl)-N-methoxymethanamine

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Reaction Steps

Reduction of 2-fluorobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of Compound 44-B gave the title hydroxylamine as a clear oil (74% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.52 (3H, s, OCH3), 4.11 (2H, s, NCH2), 5.78 (1H, broad s, NH), 7.05 (1H, m, aromatic), 7.11 (1H, m, aromatic), 7.27 (1H, m, aromatic), 7.38 (1H, m, aromatic). The hydrochloride salt was obtained as a white solid: mp 138–143° C. (dec.). Anal. calcd. for C8H10FNO—HCl: C, 50.14; H, 5.78; N, 7.31. Found: C, 50.37; H, 5.71; N, 7.18.

Provenance & Evidence