Ethyl 4-(benzyloxy)-6-methyl-1H-indole-2-carboxylate → 4-Hydroxy-2-ethoxycarbonyl-6-methylindole

HRID 903919Notes

Reaction equation

HRID 903919 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:13]2)C1C=CC=CC=1>CO.C(O)C.[Pd]>[OH:8][C:9]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:13]2

Participants

5

Reactant 1

HCID 23335518Ethyl 4-(benzyloxy)-6-methyl-1H-indole-2-carboxylate

Product 1

HCID 233354994-Hydroxy-2-ethoxycarbonyl-6-methylindole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

11.0 g of the thus obtained 4-benzyloxy-2-ethoxycarbonyl-6-methyl indole are suspended in 150 ml methanol and, after addition of a suspension of 1.0 g, 10% Pd/C in 20 ml ethanol hydrogenated at normal pressure in a duck-shaped shaking vessel. The catalyst is aspirated and the filtrate is evaporated. There is obtained pure 4-hydroxy-2-ethoxycarbonyl-6-methylindole in virtually quantitative yield.

Workup

  1. customhydrogenated at normal pressure in a duck-shaped shaking vessel
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-1f6cfef92aec45a8b98b7bcba030bc8f
Source dataset
uspto-grants-1980_10
Patent number
US04229464

Reaction notes

Loading…