5,6-Bis(phenylmethoxy)-1H-indole → 5,6-Dihydroxyindole

HRID 1735593Notes

Reaction equation

HRID 1735593 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14]C(=O)C)[NH:10][CH:9]=[CH:8]2)(=O)C.C(OC1C=C2C(=CC=1OCC1C=CC=CC=1)NC=C2)C1C=CC=CC=1>[Fe].C(O)(=O)C>[OH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[OH:14])[NH:10][CH:9]=[CH:8]2

Participants

5

Reactant 2

HCID 209205,6-Bis(phenylmethoxy)-1H-indole2×HCID 38058835,6-Diacetoxyindole

Product 1

HCID 1146835,6-Dihydroxyindole

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

In a first stage, 5,6-diacetoxyindole and 5,6-dibenzyloxyindole are prepared by means of a cyclizing reduction. In the case of 5,6-dibenzyloxyindole the cyclizing reduction is carried out using iron in the presence of acetic acid. In a second stage, 5,6-dihydroxyindole is obtained:

Sources & evidence

ORD record
ord-df9f2491c8c54926a1cae643206f11a7
Source dataset
uspto-grants-1996_07
Patent number
US05536865

Reaction notes

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