Dimethyl Sulfoxide → 2-Formylisonicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of oxalyl chloride (13.2 mL, 150 mmol) in anhydrous DCM (86 mL) under nitrogen atmosphere at −78° C. was added DMSO (21.2 mL dropwise over 20 minutes. The mixture was stirred for 15 minutes at (−78° C.) before 2-hydroxymethyl-isonicotinonitrile (4.0 g, 30 mmol) dissolved in anhydrous DCM (60 mL) was added dropwise to the reaction mixture over 5 minutes. The reaction was stirred for 2 hrs at −78° C. maintaining a nitrogen atmosphere. A white solid precipitate formed and the temperature was raised to (−55° C.) and triethylamine (6.15 mL, 450 mmol) was added dropwise for over 15 minutes, cooling bath was removed allowing the mixture to warm to room temperature over 2 hrs. The mixture was diluted with DCM (400 mL) and washed with brine (2×50 mL). The aqueous phase was extracted with DCM (3×50 mL). The combined organic layers were combined and concentrated in vacuo. A buff white solid was isolated that was used without any further purification. Single peak in LC-MS analysis, (yield taken to be quantitative), m/z (LC-MS, ESP), RT=2.53 mins, (M+H)=133.0.

Provenance & Evidence