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

HRID 900794Notes

Reaction equation

HRID 900794 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-6e5bb8cec0ca43a6bc15d7b410d21635
Source dataset
uspto-grants-2008_04
Patent number
US07361670B2

Reaction notes

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