Methyldopamine hydrochloride → 2,3-Dihydro-1-methyl-1H-indole-5,6-dione

Participants

Reaction Steps

The above-detailed manganese dioxide oxidation was effected on 50 mg (0.19 mmol) of 79% epinine hydrochloride, yielding a deep red solution of epinochrome. This was isomerized over 2.0 g water-washed Amberlyst®A-21 and 10 mL ethyl acetate. After 30 min of rapid stirring, this mixture had a slight yellowish hue. It was again Schlenk-filtered under N2, then it was partitioned. Extractions and drying as above were performed. After an identical acetylation process, 25 mg (52% yield) of DAMI was collected.

Provenance & Evidence