Water → 2-Methyl-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

2-Methylquinoline (10 g, 0.070 mol) was refluxed in 250 ml ethanol. While refluxing, sodium (22.9 g, 1.0 mol) was added cautiously over a period of 1 hour. The mixture was refluxed for an additional 3.5 hours, cooled to room temperature, poured into 500 ml H2O, and extracted 3×500 ml toluene. The organic layers were combined, dried (K2CO3) and stripped to yield title produce as an oil, 9.2 g.

Provenance & Evidence