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

HRID 2224592Notes

Reaction equation

HRID 2224592 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-5cc919b414684c64b1d50695274e024a
Source dataset
uspto-grants-2008_05
Patent number
US07378431B2

Reaction notes

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