Sodium cyanoborohydride → HCID 22485636, compound

HRID 2181130Notes

Reaction equation

HRID 2181130 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.C([BH3-])#N.[Na+]>>[F:11][C:8]1[CH:9]=[CH:10][C:5]([CH:4]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[NH:3][O:2][CH3:1])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 22485640HCID 22485640, compound

Product 1

HCID 22485636HCID 22485636, compound

Procedure

Reduction of 4,4′-difluorobenzophenone 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-dichloromethane 1:1) (41% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.49 (3H, s, OCH3), 5.18 (1H, s, NCH), 5.8 (1H, broad, NH), 7.02 (4H, m, aromatics), 7.35 (4H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 162° C. (dec). Anal. calcd for C14H13F2NO—HCl: C, 58.85; H, 4.94; N, 4.90. Found: C, 59.05; H, 4.74; N, 4.77.

Sources & evidence

ORD record
ord-ab98762fb1e74681a902f323bd0693fa
Source dataset
uspto-grants-2005_05
Patent number
US06890942B2

Reaction notes

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