Sodium cyanoborohydride → HCID 22485632, compound

HRID 2181128Notes

Reaction equation

HRID 2181128 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[CH3:5].C([BH3-])#N.[Na+]>>[F:12][C:9]1[CH:8]=[CH:7][C:6]([CH:4]([NH:3][O:2][CH3:1])[CH3:5])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 72613054HCID 72613054, compound

Product 1

HCID 22485632HCID 22485632, compound

Procedure

Reduction of 4′-fluoroacetophenone O-methyloxime with sodium cyanoborohydride as described in the preparation of 1-B gave the title hydroxylamine as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8: 2) (51% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.33 (3H, d, J=6.5 Hz, CH3), 3.46 (3H, s, OCH3), 4.12 (1H, q, J=6.5 Hz, NCH), 5.59 (1H, broad, NH), 7.02 (2H, m, aromatics), 7.32 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 99-103° C. Anal. calcd for C9H12FNO—HCl: C, 52.56; H, 6.37; N, 6.81. Found: C, 52.45; H, 6.25; N, 6.55.

Sources & evidence

ORD record
ord-5b469e3023db416abdd02fd6d10d25cc
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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