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

HRID 2223207Notes

Reaction equation

HRID 2223207 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 hydrogenated 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-ebc43dd9e2074b09b87f978ea8d23977
Source dataset
uspto-grants-2008_05
Patent number
US07375116B2

Reaction notes

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