Formaldehyde → Methyl 2-(quinolin-6-yl)acrylate

Participants

Reaction Steps

As shown in step ii of Scheme 1, methyl 2-(quinolin-6-yl)acetate (82 g, 407.5 mmol), paraformaldehyde (25.89 g, 862.1 mmol), K2CO3 (101.4 g, 733.5 mmol), and hexadecyl(trimethyl)ammonium hydrogen sulfate (15.55 g, 40.75 mmol) were taken up in toluene (1.6 liters) and refluxed for 2 hours until the starting material was completely consumed, as monitored by HPLC. The reaction mixture was cooled down using an ice-water bath and filtered through diatomaceous earth. The filtrate was washed with 1 liter of water and the organic layer dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure to afford methyl 2-(quinolin-6-yl)acrylate as a clear colorless oil (75.0 g). This material was used immediately without further purification in the next reaction.

Provenance & Evidence