Methyl 6-benzyloxy-5-nitro-indole-2-carboxylate → Methyl 5-amino-6-hydroxy-indole-2-carboxylate

HRID 896419Notes

Reaction equation

HRID 896419 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[NH:15]2)=[CH:11][C:10]=1[N+:22]([O-])=O)C1C=CC=CC=1>[Pd].O1CCCC1>[NH2:22][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:9]=1[OH:8])[NH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13]2

Participants

4

Reactant 1

HCID 16110225Methyl 6-benzyloxy-5-nitro-indole-2-carboxylate

Product 1

HCID 22350178Methyl 5-amino-6-hydroxy-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.67 g (2.0 mmol) of methyl 6-benzyloxy-5-nitro-indole-2-carboxylate, 60 ml of tetrahydrofuran and 0.1 g of 10% Pd/C catalyst is hydogenated for 5 h. The catalyst is filtered off and the filtrate containing the title compound is used immediately in the next step.

Workup

  1. filtrationThe catalyst is filtered off
  2. additionthe filtrate containing the title compound

Sources & evidence

ORD record
ord-15d573692eb34ceda25f6851342298cc
Source dataset
uspto-grants-2005_07
Patent number
US06919355B2

Reaction notes

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