Process for preparing 5,6-dihydroxyindole

Details Process for preparing 5,6-dihydroxyindole Process for preparing 5,6-dihydroxyindole

1985-10-18

1986-06-17

Lesmes, George F.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548508, C07D20926

Patent

active

045957657

ABSTRACT:
5,6-Dihydroxyindole is prepared by the catalytic reductive cyclization of 4,5-dihydroxy-2,.beta.-dinitrostyrene in a single step using hydrogen with a palladium, platinum or rhodium catalyst in a polar hydroxylic reaction system. No reaction byproducts or only a single reaction byproduct are produced. The 4,5-dihydroxy-2,.beta.-dinitrostyrene intermediate can be prepared by the chemoselective debenzylation of 4,5-dibenzyloxy-2,.beta.-dinitrostyrene using trifluoroacetic acid. 5,6-Dihydroxyindole is a useful component in hair dye formulations and as an intermediate in the synthesis of melanin.

REFERENCES:
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patent: 3732245 (1973-05-01), Batcho et al.
patent: 4255333 (1981-03-01), Opgenorth et al.
patent: 4431820 (1984-02-01), Nierenga
Benigni, J. D. et al., J. Heterocyclic Chem., 2, 387-392, (1965).

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