Reaktion #45565

Reaktionsgleichung

3-fluoro-2-methoxy-5-methylaniline

hydrochloric acid

trichloroacetaldehyde monohydrate

magnesium sulfate

N,N-dimethylformamide

hydroxylamine hydrochloride

→

compound

Ausbeute 10.0%

(3-Fluoro-2-methoxy-5-methylphenyl)-2-hydroxyimino-acetamide

Ausbeute 10.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring at the same temperature for 13 hours
2. 2
   TemperaturAfter cooling to room temperature
3. 3
   Sonstigethe reaction liquid
4. 4
   Filtrationwas filtered through Celite
5. 5
   Extraktionthe filtrate was extracted three times with ethyl acetate
6. 6
   Waschenthe organic layer was washed twice with saturated brine
7. 7
   Trocknendried over anhydrous magnesium sulfate
8. 8
   FiltrationAfter filtration and concentration under reduced pressure
9. 9
   Einengenthe eluate with chloroform was concentrated under reduced pressure

Vorschrift

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.

Quelle