Hydrochloric Acid → 2-Phenyl-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

2-Phenylquinoline (65 g) was dissolved in absolute alcohol (200 ml) and heated to reflux when sodium metal (25 g) was added in portions over 1 hr. The resulting mixture was maintained at reflux for a further 3 hr. The mixture was diluted with water (300 ml) and acidified with conc. hydrochloric acid. The alcohol was removed in vacuo and the residue made basic with 10M sodium hydroxide solution. The resulting solution was extracted with ether (4×150 ml) and the ether layer was dried (magnesium sulphate) and evaporated in vacuo to give an oil which was distilled twice to give the product, 1,2,3,4-tetrahydro-2-phenylquinoline (b.pt. 114°/0.1 mm Hg). This was characterised by its nmr spectrum.

Provenance & Evidence