Sodium Hydroxide → N-(3,4-dichloro-benzyl)-O-methyl-hydroxylamine

To methoxylamine hydrochloride (20 g, 0.24 mol) in water (200 mL) and THF (74 mL) was added sodium acetate (16.3 g, 0.2 mol) followed by 3,4-dichlorobenzaldehyde (25 g, 0.14 mol). The mixture was stirred at room temp for 6 h and diluted with diethyl ether. The aqueous phase was extracted with ethyl acetate, dried (sodium sulfate) and concentrated to give a colorless oil. The oil was dissolved in glacial acetic acid (200 mL) and cooled to 0° C. Sodium cyanoborohydride (18.8 g, 0.26 mol) was added over 30 min. The mixture was stirred at room temp for 4 days, cooled to 0° C. and made basic with 10 N NaOH. The mixture was extracted with EtOAc (3×'s) and the combined organic extracts were washed with water and brine and concentrated to give an oil that solidifies upon standing. This residue was stirred in diethyl ether and the resulting title compound was filtered as a white solid (9.61 g, 33% yield). 1HNMR (300 MHz, DMSO) δ: 10.12 (1H, bs), 7.74 (1H, s), 7.67 (1H, d, J=8.42 Hz), 7.44 (1H, d, J=8.05 Hz), 4.21 (2H, s), 3.59 (3H, s).

1. extractionThe aqueous phase was extracted with ethyl acetate
2. dry with materialdried (sodium sulfate)
3. concentrationconcentrated
4. customto give a colorless oil
5. temperaturecooled to 0° C
6. stirringThe mixture was stirred at room temp for 4 days
7. temperaturecooled to 0° C.
8. extractionThe mixture was extracted with EtOAc (3×'s) and the combined organic extracts
9. washwere washed with water and brine
10. concentrationconcentrated
11. customto give an oil that

ORD record

ord-7239081edaa34cb7a4361af5446944e9

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109186B2