Hydrochloric Acid → N-[(2-Fluoro-6-methoxyphenyl)methylidene]hydroxylamine

Participants

Reaction Steps

To a flask charged with 2-fluoro-6-methoxylbenzaldehyde (Compound A, 2.43 g, 15.8 mmol) and hydroxylamine hydrochloride (“NH2OH. HCl”, 1.21 g, 17.3 mmol) in ethanol (60 mL) and H2O (120 mL) was added aq. NaOH (50% w/w 3.2 mL). The reaction mixture was stirred at room temperature for 1 hour. At the conclusion of this period, the reaction was neutralized with concentrated HCl to pH 7 and then extracted with methylene chloride (“CH2Cl2”, 3×200 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4 and filtered. The volatiles were removed under reduced pressure to provide 2-fluoro-6-methoxybenzaldehyde oxime, Compound B, as a white solid (2.45 g, 92%). m/z (ES+) 169 (M+H).

Provenance & Evidence