Sodium Hydroxide → HCID 86739742, compound

Participants

Reaction Steps

To (±)-8-hydroxy-1-methyl decahydroquinoline (D.14)3 (24.3 g), dissolved in 7M aqueous sulphuric acid (140 ml), at 0°, was added chromium trioxide (15.2 g), dissolved in 7M aqueous sulphuric acid (270 ml) over a period of 1/2 h, with stirring. After stirring for an additional 1 hr at room temperature, the solution was made basic with 40% sodium hydroxide solution, and the aqueous phase was extracted with chloroform (3×600 ml). The combined organic extracts were dried (K2CO3) and evaporated under reduced pressure. The resulting cis, trans-quinolinone was dissolved in absolute methanol (200 ml) and treated with sodium methoxide (ca 0.8 g). After 72 hr at room temperature, the solvent was removed under reduced pressure and the product was partitioned between chloroform and saturated aqueous potassium carbonate. Distillation of the organic extracts gave (±)-1-methyl-trans-decahydro-8-quinolinone (D.15) (8.69, 36%). (This product contained a small quantity (<20%) of the corresponding cis isomer).

Provenance & Evidence