Sodium cyanoborohydride → o-Methyl-n-(4-trifluoromethyl-benzyl)-hydroxylamine

HRID 1836523Notes

Reaction equation

HRID 1836523 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.C([BH3-])#N.[Na+]>>[CH3:1][O:2][NH:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 740573304-Trifluoromethyl-benzaldehyde o-methyloxime

Product 1

HCID 23499567o-Methyl-n-(4-trifluoromethyl-benzyl)-hydroxylamineYield 73%

Procedure

Reduction 4-trifluoromethyl-benzaldehyde O-methyloxime of with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil (73% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.49 (3H, s, OCH3), 4.09 (2H, s, NCH2), 5.80 (1H, broad s, NH), 7.48 (2H, m, aromatics), 7.60 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 132-133° C. Anal. calcd for C9H10F3NO—HCl: C, 44.74; H, 4.59; N, 5.80. Found: C, 44.71; H, 4.53; N, 5.68.

Sources & evidence

ORD record
ord-7079051ca95344a59a1c3734277db018
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

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