Dimethyl Sulfoxide → 4-(7-Chloroquinolin-4-yl)butyraldehyde

HRID 1274409Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

Oxalyl chloride (0.42 mL of a 2M solution in dry methylene chloride) was placed in an oven-dried flask, cooled to -78° C. and a solution of 99 mg methylsulfoxide in dry methylene chloride (2 mL) added drop by drop to the oxalyl chloride over 3 minutes and stirred for a further 3 minutes. A solution of 4-(7-chloroquinolin-4-yl)butan-1-ol (100 mg) in dry methylene chloride (1 mL) was added to the reaction flask over approx. 3 minutes followed by anhydrous triethylamine (0.42 mL) and the reaction mixture stirred for another 2.5 hours during which time it was allowed warmed up to room temperature. The reaction was quenched by the addition of saturated brine and then partitioned with methylene chloride. The aqueous layer was discarded and the methylene chloride extract dried over anhydrous sodium sulfate powder, filtered and concentrated in vacuo. The title compound was isolated by flash chromatography on silica gel (ethyl acetate:hexane, 2:1; then ethyl acetate), 57 mg.

Workup

stirringthe reaction mixture stirred for another 2.5 hours during which time it
temperaturewas allowed warmed up to room temperature
customThe reaction was quenched by the addition of saturated brine
custompartitioned with methylene chloride
extractionthe methylene chloride extract
dry with materialdried over anhydrous sodium sulfate powder
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-cb0d1846999c48b7b3ba7a03c6b96910
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156767

Reaction notes

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