Hydrochloric Acid → 2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Participants

Reaction Steps

A solution of 0.364 g (2.07 mmol) of 3-carboxy-1,2,3,4-tetrahydroisoquinoline in 25 mL of formic acid was combined with 2.5 mL of 37% formaldehyde. The resulting mixture was allowed to reflux for approximately 17 hours. After cooling, the mixture was contentrated under reduced pressure to provide a gum. This gum was dissolved in 3.0 mL of water, adjusted to a pH 2 using hydrochloric acid and then purified using ion-exchange chromatography (Dowex 50x-8, 100 meshcation) to provide 0.21 g of a yellow powder.

Provenance & Evidence