Triethylamine → 6-Chloro-4-(4-fluorophenyl)-2-methyl-3-quinolinecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (8.85 mL, 1.1 equivalents) in 150 mL of dry dichloromethane at -78° C. under nitrogen, was added dropwise a solution of dimethylsulfoxide (14.2 mL, 2.2 equivalents) in 125 mL of dichloromethane. After complete addition, the mixture was stirred for five minutes at -78° C. and then a solution of 6-chloro-4-(4-fluorophenyl)-2-methyl-3-quinolinemethanol (27.8 ) in 100 mL of dichloromethane and 50 mL of dimethylsulfoxide was added dropwise. This solution was stirred at -78° C. for one hour, after which triethylamine (64.1 mL, 5.0 equivalents) was added. The cooling bath was removed and 400 mL of saturated ammonium chloride solution was added to the reaction mixture.

Provenance & Evidence