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

HRID 902144Notes

Reaction equation

HRID 902144 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-4b43da8d37c94be98d21d1370b73c0ab
Source dataset
uspto-grants-2008_04
Patent number
US07365083B2

Reaction notes

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