Ethyl 4-(phenylmethoxy)-1H-indole-2-carboxylate → Ethyl 4-hydroxy-1H-indole-2-carboxylate

HRID 1929035Notes

Reaction equation

HRID 1929035 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15]CC1C=CC=CC=1)[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]>CO.C(Cl)Cl.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([OH:15])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 119707Ethyl 4-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 13274763Ethyl 4-hydroxy-1H-indole-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-Benzyloxy-1H-indole-2-carboxylic acid ethyl ester (29 g, 98.2 mmol) in a mixture of MeOH (750 ml) and DCM (500 ml) is added 1 gram of Pd/C (10%). It is hydrogenated under normal pressure for 24 hours. After filtration and evaporation a white powder is obtained.

Workup

  1. filtrationAfter filtration and evaporation a white powder
  2. customis obtained

Sources & evidence

ORD record
ord-e1153987325d4679ad3deb1d89a3bb3c
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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