Aluminum(III) Chloride → HCID 23369592, compound

Participants

Reaction Conditions

Reaction Steps

N-(2-Brom-5-methoxyphenyl)-3,3-dimethylacrylamide (530 mg, 1.87 mmol) was dissolved in m-dichlorobenzene (10 ml). To the resultant solution, aluminum chloride (1.24 g, 9.33 mmol) was added, and the mixture was stirred at 120° C. for 40 minutes. The reaction mixture was poured into ice-water, followed by extracting with chloroform-methanol (10:1), and drying. Subsequently, the residue was subjected to silica gel column chromatography (developer=chloroform-methanol =30:1). From the first eluate, 152 mg of 4,4-dimethyl-5-hydroxy-3,4-dihydrocarbostyril (152 mg, 42.5%) was obtained as pale yellow needles. From the second eluate, 4,4-dimethyl-7-hydroxy-3,4-dihydrocarbostyril (63 mg, 17.6%) was obtained as pale yellow needles.

Provenance & Evidence