Ethanol → 5-Amino-2-methylindole

HRID 725957

Reaction equation

HRID 725957 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.C(O)C.[H][H]>[Pd].O1CCCC1>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH2:11])=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 702EthanolHCID 2803132-Methyl-5-nitro-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 27339925-Amino-2-methylindoleYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.0 gm (11.4 mMol) 2-methyl-5-nitro-1H-indole in 100 mL 1:1 ethanol:tetrahydrofuran were added 0.25 gm 5% palladium on carbon. The suspension was hydrogenated at ambient temperature at an initial hydrogen pressure of 60 p.s.i. After 5 hours the reaction mixture was filtered and the filtrate concentrated under reduced pressure to give 1.5 gm of a dark brown solid. The solid was purified by flash chromatography, eluting with a gradient of dichloromethane containing 0-3% methanol, to give 1.19 gm (71.7%) of the title compound as light brown plates.

Workup

  1. filtrationAfter 5 hours the reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-873572327a76493ebceb04d83056d8b6
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Linked notes

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