Formaldehyde → 1,8-Dimethyl-1,2,3,4-tetrahydroquinoline-5-carboxylic acid

Participants

Reaction Steps

24 mmol of sodium cyanoborohydride were added to 5 mmol of 8-methyl-1,2,3,4-tetrahydroquinoline-5-carboxylic acid and 50 mmol of paraformaldehyde in 30 ml of glacial acetic acid, the temperature being kept below 30° C. using an ice bath. The mixture was stirred at room temperature for 15 hours and then poured onto ice and adjusted to pH 4 using aqueous sodium hydroxide solution. The mixture was then extracted with ethyl acetate and the organic phase was washed with water, dried over sodium sulfate and concentrated.

Provenance & Evidence