Sodium cyanoborohydride → 2,4-Difluoro-N-methoxybenzenemethanamine

HRID 2214600Notes

Reaction equation

HRID 2214600 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12].C([BH3-])#N.[Na+]>>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[CH2:4][NH:3][O:2][CH3:1]

Participants

3

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 73855574HCID 73855574, compound

Product 1

HCID 219474102,4-Difluoro-N-methoxybenzenemethanamineYield 72%

Procedure

Reduction of 2,4-difluorobenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of Compound 44-B gave the title hydroxylamine as a clear oil (72% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.51 (3H, s, OCH3), 4.07 (2H, s, NCH2), 6.78–6.88 (2H, m, aromatics), 7.32–7.38 (1H, m, aromatic). The hydrochloride salt was obtained as a white solid: mp 154–158° C. (dec.). Anal. calcd. for C8H9NO2—HCl: C, 45.83; H, 4.80; N, 6.68. Found: C, 45.81; H, 4.84; N, 6.59.

Sources & evidence

ORD record
ord-6a192d4dd8ff4c4aab99e4e7c6be636f
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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