Acryloyl chloride → HCID 22485556, compound

Participants

Reaction Steps

To a solution of 5-amino-2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]pyridine (melting point: 176.0-177.5° C.)(28.2 g, 85.4 mmol) synthesized by a similar procedure to that described in Reference Example 11 in methylene chloride (550 mL) was added N,N-diisopropylethylamine (18.0 mL, 103 mmol). To the ice-cold stirred solution was added acryloyl chloride (7.00 mL, 86.0 mmol) dropwise over about 10 minutes. A saturated aqueous sodium hydrogencarbonate was added, and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Chloroform-hexane (1:2, 300 mL) was added to the residue and the resulting precipitate was collected by filtration to yield crude 5-acryloylamino-2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]pyridine was obtained as colorless needles (melting point: 207.0-209.0° C.)(38.2 g).

Provenance & Evidence