1H-Indole-2-carboxylic acid, 1-methyl-5-(phenylmethoxy)-, ethyl ester → Ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylate

HRID 21597Notes

Reaction equation

HRID 21597 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11]CC3C=CC=CC=3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[OH:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[C:3]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4]2

Participants

3

Reactant 1

HCID 114836801H-Indole-2-carboxylic acid, 1-methyl-5-(phenylmethoxy)-, ethyl ester

Product 1

HCID 15365972Ethyl 5-hydroxy-1-methyl-1H-indole-2-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared from ethyl 1-methyl-5-(phenylmethoxy)-1H-indole-2-carboxylate (Monge Vega A, et al., An. Ouim. 72:267) by catalytic hydrogenolysis in ethanol as described in Example 15. Recrystallization from ether gives the product in 80% yield; mp 140°-142° C.

Workup

  1. customRecrystallization from ether
  2. customgives the product in 80% yield

Sources & evidence

ORD record
ord-ba46a826d6e6487bac0d0fa08f6fa94b
Source dataset
uspto-grants-1995_06
Patent number
US05424329

Reaction notes

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