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

HRID 1836526Notes

Reaction equation

HRID 1836526 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[C:12]([F:15])([F:14])[F:13].C([BH3-])#N.[Na+]>>[F:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH:3][O:2][CH3:1])=[C:6]([C:12]([F:13])([F:14])[F:15])[CH:7]=1

Participants

3

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 740573284-Fluoro-2-trifluoromethyl-benzaldehyde o-methyloxime

Product 1

HCID 23499553n-(4-Fluoro-2-trifluoromethyl-benzyl)-o-methyl-hydroxylamine

Procedure

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.

Sources & evidence

ORD record
ord-86fb66e5c7844adbacf9cafe016b1e37
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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