Methyl 6-benzyloxy-5-nitro-indole-2-carboxylate → Methyl 5-amino-6-hydroxy-indole-2-carboxylate
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]2Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- filtrationThe catalyst is filtered off
- 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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