Hydrogen Bromide → N-(4-Oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(1,2,3,4-tetrahydro-1-naphthyl)-acetamide (30 g), cobaltous acetate tetrahydrate (13.12 g), 30% hydrobromic acid in acetic acid (4.28 g), methyl isobutyl ketone (400 ml) and acetic acid (100 ml) is stirred and oxygen is introduced via a capillary gas dispersion tube. The mixture is heated gradually to 62° C. and the reaction is run 17 hours at 62° C. The reaction mixture is then cooled, the oxygen flow terminated and water (500 ml) is added. The mixture is extracted with chloroform (500 ml and 2×300 ml), the chloroform extracts are combined, washed with saturated sodium chloride solution and evaporated to dryness in vacuo. Benzene (200 ml) is added to the residue, the solution is filtered and the filtrate evaporated to dryness in vacuo to afford 40.3 g (damp) of the title compound.

Provenance & Evidence