Pyridine → HCID 67247801, compound

Participants

Reaction Conditions

Reaction Steps

1.03 g of 2-(4-bromopyridin-2-yl)-1-p-tolylethanone obtained in step 13.1 are placed in a round-bottomed flask with 0.99 g (14.2 mmol) of hydroxylamine monohydrochloride, 3 mL (37 mmol) of pyridine and 100 mL of ethanol. The reaction medium is stirred overnight and then concentrated under reduced pressure. The residue obtained is then taken up in 200 mL of ethyl acetate and 200 mL of water. The organic phase is recovered, dried over sodium sulfate and then concentrated under reduced pressure. 1.10 g of compound are recovered and dissolved in a round-bottomed flask containing 0 660 mL (4.74 mmol) of triethylamine and 30 mL of dichloromethane. The reaction medium is then cooled to about 5° C. and 0.200 mL (1.42 mmol) of trifluoroacetic anhydride is added dropwise. The medium is then stirred at room temperature for 3 hours, followed by hydrolysis with 100 mL of water. The medium is then stirred for 10 minutes, followed by filtration through a hydrophobic cartridge (Radleys® 70 mL liquid/liquid extraction column). 1.2 g of silica are then added to the filtrate, followed by concentrating under reduced pressure. The powder obtained is used as a solid deposit for a chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (95/5). 0.746 g (77%) of expected compound is recovered in the form of a white powder.

Provenance & Evidence