Hydrogen Bromide → HCID 22405796, compound

Participants

Reaction Steps

A 0.90 g quantity of sodium nitrite was added to a solution of 3.30 g of 4-[3-(2-pyridyl)-2-oxooxazolidin-5-yl]methoxyaniline obtained in Reference Example 21 in 40 ml of methanol, 10 ml of acetone and 8.0 g of 47% hydrobromic acid. The mixture was stirred with ice-cooling for 0.5 hour. To the mixture was added 6.4 ml of methyl acrylate, and 256 mg of cuprous oxide was added thereto at 40° C. and the mixture was stirred at the same temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure and the obtained residue was extracted with ethyl acetate. The extract was washed successively with aqueous ammonia and an aqueous solution of sodium chlorides, dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and purified by hexane-ethyl acetate gradient elution to give 2.7 g of the title compound (compound 196) as an oil (yield 53%).

Provenance & Evidence