Acetic Acid → 1,2,3,4-Tetrahydro-1-methylquinoline

Participants

Reaction Steps

1,2,3,4-tetrahydroquinoline (2.0 g, 0.0015 mol) and formaldehyde (12 ml of 38% aqueous, 0.015 mol) were combined in 60 ml CH3CN. NaBH3CN (2.85 g) and then, over a 10 minute period, glacial acetic acid (1.50 ml) were added and the mixture stirred 2 hours, at which time additional acetic acid (0.5 ml) was added. After stirring an additional 30 minutes, the reaction mixture was poured into 200 ml ether, washed 3×30 ml IN NaOH, dried (K2CO3) and stripped in vacuo to yield title product, 2.27 g.

Provenance & Evidence