Hydrochloric Acid → (3-Fluoro-2-methoxy-5-methylphenyl)-2-hydroxyimino-acetamide

Temperature

90 °C

A N,N-dimethylformamide (30 ml) solution of 3-fluoro-2-methoxy-5-methylaniline (I-26) (4.31 g, 27.8 mmol) and concentrated hydrochloric acid (3.5 ml, 33.4 mmol) were added to a water (60 ml) suspension of trichloroacetaldehyde monohydrate (9.2 g, 55.6 mmol) and anhydrous magnesium sulfate (31.6 g, 222.4 mmol), followed by stirring at 90° C. for 30 minutes, then hydroxylamine hydrochloride (116 g, 166.8 mmol) was added, followed by stirring at the same temperature for 13 hours and a half. After cooling to room temperature, the reaction liquid was filtered through Celite, the filtrate was extracted three times with ethyl acetate, then the organic layer was washed twice with saturated brine, dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform was concentrated under reduced pressure to obtain the entitled compound (596 mg, 10%) as a pale brown solid.

1. stirringby stirring at the same temperature for 13 hours
2. temperatureAfter cooling to room temperature
3. customthe reaction liquid
4. filtrationwas filtered through Celite
5. extractionthe filtrate was extracted three times with ethyl acetate
6. washthe organic layer was washed twice with saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationAfter filtration and concentration under reduced pressure
9. concentrationthe eluate with chloroform was concentrated under reduced pressure

ORD record

ord-7aa9800923944b4e93b12b5d5e042baf

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737166B2