Sodium Hydroxide → 1-methyl-1H-indol-5-amine

HRID 450041Notes

Reaction equation

HRID 450041 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.O.[Sn](Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1473221H-Indole, 1-methyl-5-nitro-HCID 43835034Tin dichloride dihydrate

Product 1

HCID 27695641-methyl-1H-indol-5-amineYield 28.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1-methyl-5-nitro-1H-indole (0.5 g, 2.84 mmol) in ethyl acetate (10 ml), tin (II) chloride hydrate (2.5 g, 11.4 mmol, 4 eq) was added and the reaction mixture stirred overnight at room temperature. The reaction mixture was basified with aqueous sodium hydroxide solution (pH 8) and the compound extracted using ethyl acetate. The crude compound obtained was purified by column chromatography over silica gel using ethyl acetate/hexane (1:1) as eluent to give 1-methyl-1H-indol-5-ylamine (120 mg, 27%).

Workup

  1. extractionthe compound extracted
  2. customThe crude compound obtained
  3. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-f2a51d32b9ed447884bbcdbf7db23b96
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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