Sodium cyanoborohydride → BENZENEMETHANAMINE, 3-FLUORO-N-METHOXY-

HRID 2214553Notes

Reaction equation

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

Participants

Reactant 2

HCID 5003444Sodium cyanoborohydride

HCID 73855580HCID 73855580, compound

Product 1

HCID 12146886BENZENEMETHANAMINE, 3-FLUORO-N-METHOXY-Yield 60%

Procedure

Reduction 3-fluorobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of Compounds 44-A and 44-B gave the title hydroxylamine as a clear oil (60% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.50 (3H, s, OCH3), 4.04 (2H, s, NCH2), 5.75 (1H, broad s, NH), 6.95–7.32 (4H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 130–131° C. (dec.). Anal. calcd for C8H10FNO—HCl: C, 50.14; H, 5.78; N, 7.31. Found: C, 50.10; H, 5.73; N, 7.38.

Sources & evidence

ORD record: ord-70878150ba744a7eb6f2f45fef353917
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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