8-Hydroxy-5,6,7,8-tetrahydroquinoline → 6,7-Dihydro-5H-quinoline-8-one

Participants

Reaction Steps

To a stirred solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline (13.96 g, 93.6 mmol) in dry CH2Cl2 (400 mL) was added solid <5 micron activated 85% MnO2 (manganese IV oxide) (82.22 g, 804 mmol). The resulting black suspension was stirred 18 h, at which point the mixture was filtered through a cake of celite and washed with CH2Cl2 (3×50 mL). The combined washings were concentrated to provide 11.27 g (82%) of the title compound as a pale yellow solid, which was used in subsequent reactions without further purification. This material displayed spectra identical to those reported above.

Provenance & Evidence