Sodium cyanoborohydride → HCID 22485637, compound
Reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([CH3:12])[CH:6]=1.C([BH3-])#N.[Na+]>>[F:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][NH:3][O:2][CH3:1])=[CH:6][C:7]=1[CH3:12]Participants
3
Procedure
Reduction of 4-fluoro-3-methyl-benzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 1-B gave the title hydroxylamine as a clear oil after chromatography on silica gel (elution hexane-ethyl acetate 8: 2) (94% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 2.27 (3H, broad s, CH3), 3.50 (3H, s, OCH3), 3.97 (2H, broad s, NCH2), 5.67 (1H, broad, NH), 6.95 (1H, m, aromatic), 7.11-7.17 (2H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 162° C. Anal. calcd for C9H12FNO—HCl: C, 52.56; H, 6.37; N, 6.81. Found: C, 52.80; H, 6.33; N, 6.70.
Sources & evidence
- ORD record
- ord-7c1ea588e77b442ebc39e0949d5f8199
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06890942B2
Reaction notes
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