Iodoacetamide → 1,3,4,5-tetrahydro-6-methoxy-2H-benzo[e]indol-2-one

Participants

Reaction Steps

439 g (2.49 mol) of 5-methoxy-2-tetralone and 227 ml (3.67 mol) of pyrrolidine were dissolved in 3 l of toluene. After the addition of 16.4 g (0.09 mol) of p-toluenesulfonic acid monohydrate the mixture was boiled for 4 hours, whereby the resulting water was removed continuously using a water separator. Thereupon, the toluene was distilled off in a vacuum. The residue was dissolved in 1 l of tetrahydrofuran, whereupon a solution of 500 g (2.70 mol) of iodoacetamide in 2.5 l of tetrahydrofuran was added dropwise at room temperature. The mixture was boiled at reflux for 30 minutes, then cooled to room temperature and stirred for a further 12 hours. The solid was filtered off and washed with tetrahydrofuran. There were obtained 475 g (89%) of 1,3,4,5-tetrahydro-6-methoxy-2H-benzo[e]indol-2-one as white crystals with m.p. 220°-222°.

Provenance & Evidence