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

Participants

Reaction Steps

The above-detailed manganese dioxide oxidation was effected on 51 mg (0.20 mmol) 79% epinine hydrochloride, yielding a deep red solution of epinochrome. This was isomerized over a mixture of 0.56 g (2.5 mmol) of zinc acetate and 15 mL of ethyl acetate. After 45 min of rapid stirring, this mixture was yet slightly pink. It was again Schlenk-filtered under N2, then it was partitioned. Extractions and drying were performed as in Example 5. After an identical acetylation process, 31 mg (63% yield) of DAMI was collected.

Provenance & Evidence