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

HRID 34295Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH3:18])[C:12]([CH2:19][OH:20])=[C:11]2[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1.C(N(CC)CC)C>ClCCl.CS(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH3:18])[C:12]([CH:19]=[O:20])=[C:11]2[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

additionAfter complete addition
stirringThis solution was stirred at -78° C. for one hour
customThe cooling bath was removed
addition400 mL of saturated ammonium chloride solution was added to the reaction mixture

Sources & evidence

ORD record: ord-52f922d09f9940b58a36c945d1a4e891
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04761419

Reaction notes

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