Sodium cyanoborohydride → HCID 21947562, compound

HRID 2214589Notes

Reaction equation

HRID 2214589 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([Br:12])[CH:6]=1.C([BH3-])#N.[Na+]>>[Br: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

3

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 73855553HCID 73855553, compound

Product 1

HCID 21947562HCID 21947562, compoundYield 83%

Procedure

Reduction of 3-bromo-4-fluorobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of Compound 44-B gave the title hydroxylamine as a clear oil (83% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.48 (3H, s, OCH3), 3.99 (2H, s, NCH2), 7.08 (1H, m, aromatic), 7.27 (1H, m, aromatic), 7.57 (1H, m, aromatic). The hydrochloride salt was obtained as a white solid: mp 150–151° C. Anal. calcd. for C8H9BrFNO—HCl: C, 35.52; H, 3.73; N, 5.18. Found: C, 35.54; H, 3.61; N, 5.12.

Sources & evidence

ORD record
ord-62d3cea39f35474194b9eb8c5b4b4178
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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