Sodium cyanoborohydride → HCID 12146889, compound

HRID 2214576Notes

Reaction equation

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

Participants

Reactant 2

HCID 5003444Sodium cyanoborohydride

HCID 73855547HCID 73855547, compound

Product 1

HCID 12146889HCID 12146889, compoundYield 82%

Procedure

Reduction of 3,4-difluorobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of Compound 44-B gave the title hydroxylamine as a clear oil (82% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.48 (3H, s, OCH3), 3.98 (2H, s, NCH2), 5.73 (1H, broad s, NH), 7.04–7.23 (3H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 139–142° C. (dec.). Anal. calcd. for C8H9F2NO2—HCl: C, 45.83; H, 4.80; N, 6.68. Found: C, 45.96; H, 4.93, N, 6.67.

Sources & evidence

ORD record: ord-4391e52e34a54c08800d0f3e3deb66ac
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

Loading…