2-Methyl-5-nitro-1H-indole → 5-Amino-2-methylindole

HRID 454200

Reaction equation

HRID 454200 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([N+:11]([O-])=O)=[CH:6][CH:5]=2.[H][H]>C(O)C.C1COCC1.[Pd]>[NH2:11][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2]([CH3:1])=[CH:10]2

Participants

6

Reactant 2

HCID 2803132-Methyl-5-nitro-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 27339925-Amino-2-methylindoleYield 99.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methyl-5-nitroindole (1 g, 5.7 mmol) in ethanol (25 ml) and THF (25 ml) containg 10% palladium on charcoal (128 mg) was hydrogenated until uptake of hydrogen ceased. The mixture was filtered and the filtrate was evaporated to give 5-amino-2-methylindole (830 mg, quant.).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-fa041f888df349298ff5b641bf002f5e
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Linked notes

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