Ethyl 4-benzyloxy-1-methylindole-2-carboxylate → Ethyl 4-hydroxy-1-methyl-1H-indole-2-carboxylate

HRID 460552Notes

Reaction equation

HRID 460552 reaction equation
C([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:13]2[CH3:18])C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:13]2[CH3:18]

Participants

4

Reactant 1

HCID 22054863Ethyl 4-benzyloxy-1-methylindole-2-carboxylate

Product 1

HCID 10130663Ethyl 4-hydroxy-1-methyl-1H-indole-2-carboxylateYield 86.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution (200 ml) of ethyl 4-benzyloxy-1-methylindole-2-carboxylate (13.0 g) in ethanol was added 10% palladium-carbon (1.3 g), and the mixture was stirred at room temperature for 8 hr under a hydrogen atmosphere. The palladium-carbon was filtered off with celite and the reaction mixture was concentrated under reduced pressure to give the title compound (8.0 g) as a brown oil.

Workup

  1. filtrationThe palladium-carbon was filtered off with celite
  2. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c60d4ca8a50741dcb5ad46201c841ffb
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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