O-Methylhydroxylamine hydrochloride → 3-(4-Fluorophenyl)-propionaldehyde o-methyloxime

HRID 1836538Notes

Reaction equation

HRID 1836538 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=O)=[CH:4][CH:3]=1.Cl.[O:13]([NH2:15])[CH3:14]>>[CH3:14][O:13][N:15]=[CH:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 101977823-(4-Fluorophenyl)propanal

Product 1

HCID 739889653-(4-Fluorophenyl)-propionaldehyde o-methyloximeYield 97%

Procedure

Reaction of 3-(4-fluorophenyl)-propionaldehyde (Dickinson, R. P.; Dack, K. N.; Steele, J.; Tute, M. S. Bioorg. Med. Chem. Lett., 6, 14, 1996, 1691-1696) with methoxylamine hydrochloride as described in the preparation of compound 3-A gave the title oxime ether as a clear oil (97% yield), bp 65-75° C./1.5 torr (bulb to bulb distillation, air bath temperature). 1HNMR indicated a 6:4 mixture of E- and Z-isomers. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.51 and 2.65 (2H, 2 m, CH2), 2.8 (2H, m, CH2), 3.84 and 3.88 (3H, 2 s, OCH3), 6.67 (t, J=5.5 Hz, CH), 7.0 (2H, m, aromatics), 7.16 (2H, m, aromatics), 7.40 (t, J=4.2 Hz, CH).

Workup

  1. customgave

Sources & evidence

ORD record
ord-2987aec28334415f9f2470f40af3b0f4
Source dataset
uspto-grants-2004_08
Patent number
US06777440B2

Reaction notes

Loading…