Thionyl Chloride → 8-Chloro-3-methyl-5,6,7,8-tetrahydroquinoline hydrochloride

Participants

Reaction Conditions

Reaction Steps

The 8-hydroxy product of Example 1 (15 g.) was added portionwise to thionyl chloride (33 g.) at 0° C and the mixture stirred at 0° C for 1 hour and heated at reflux for an additional 2 hours. The solvent was removed in vacuo and the residual oil heated at reflux for 1 hour with ethanol (15 ml.) to remove excess thionyl chloride. The resultant precipitate was recrystallised from ethanol-ether to give 8-chloro-3-methyl-5,6,7,8-tetrahydroquinoline hydrochloride as colourless needles (17.4 g.) m p. 177° C. (Found: C, 55.3; H, 6.1; N, 6.5 C10H12C1N.HC1 requires: C,55.1; H,6.0; N, 6.4%).

Provenance & Evidence