Sodium cyanoborohydride → n-(4-Fluoro-2-trifluoromethyl-benzyl)-o-methyl-hydroxylamine

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Reduction of 4-fluoro-2-trifluoromethyl-benzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8:2) (35% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.55 (3H, s, OCH3), 4.21 (2H, s, NCH2), 5.76 (1H, broad, NH), 7.26 (1H, m, aromatic), 7.38 (1H, m, aromatic), 7.64 (1H, m, aromatic). The hydrochloride salt was obtained as a white solid: mp 138-140° C. Anal. calcd for C9H9F4NO—HCl: C, 41.64; H, 3.88; N, 5.39. Found: C, 41.49; H, 3.68; N, 5.26.

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