Sodium cyanoborohydride → 1-(2-Fluorophenyl)-N-methoxymethanamine
Reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11].C([BH3-])#N.[Na+]>>[F:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][NH:3][O:2][CH3:1]Participants
3
Procedure
Reduction of 2-fluorobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of compound 3-B gave the title hydroxylamine as a clear oil (74% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.52 (3H, s, OCH3), 4.11 (2H, s, NCH2), 5.78 (1H, broad s, NH), 7.05 (1H, m, aromatic), 7.11 (1H, m, aromatic), 7.27 (1H, m, aromatic), 7.38 (1H, m, aromatic). The hydrochloride salt was obtained as a white solid: mp 138-143° C. (dec.). Anal. calcd. for C8H10FNO—HCl: C, 50.14; H, 5.78; N, 7.31. Found: C, 50.37; H, 5.71; N, 7.18.
Sources & evidence
- ORD record
- ord-28aaf0b460964d9485970eaf6ea290bd
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06777440B2
Reaction notes
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