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

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).

1. extractionextracted with methylene chloride (“CH2Cl2”, 3×200 mL)
2. washThe combined organic layers were washed with brine (100 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. customThe volatiles were removed under reduced pressure

ORD record

ord-d66eaa1d609746ecaa675d38dd664ebc

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357809B2