m-Chloroperbenzoic acid → 3-Methyl-5,6-dihydroquinoline

Participants

Reaction Steps

A solution of the crude product of Step 1 (4.2 g, 13.9 mmol) in dichloromethane (100 ml) at -40° was treated portionwise with 86% 3-chloroperoxybenzoic acid (3.0 g, 14.9 mmol). After 30 min, the mixture was warmed to room temperature, washed with 2N-NaOH (2×100 ml), dried (MgSO4), and evaporated in vacuo. The residue was dissolved in 1N-H2SO4 (100 ml) and the solution washed with ether (3×100 ml), basified with sodium carbonate, and extracted with dichoromethane (3×100 ml). The chlorinated extracts were dried (MgSO4) and evaporated in vacuo. The residue was distilled to give the product (1.79 g) as an oil.

Provenance & Evidence