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

HRID 728387Notes

Reaction equation

HRID 728387 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([OH:12])[CH:6]=1.Cl>[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:8]([CH:9]=2)=[O:11])=[O:12])[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 86470Methyldopamine hydrochloride

Product 1

HCID 123096132,3-Dihydro-1-methyl-1H-indole-5,6-dioneYield 63%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

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.

Sources & evidence

ORD record
ord-f12d7351907f486a86e3eed54fb1aa21
Source dataset
uspto-grants-1991_09
Patent number
US05047592

Reaction notes

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