Sodium Hydroxide → 1-Methylindolin-5-amine

HRID 450045Notes

Reaction equation

HRID 450045 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)[CH2:4][CH2:3]1.[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)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1677381H-Indole, 2,3-dihydro-1-methyl-5-nitro-

Product 1

HCID 226371221-Methylindolin-5-amineYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-methyl-5-nitro-2,3-dihydro-1H-indole (0.2 g, 1.13 mmol) in ethyl acetate (12 ml) was added stannous chloride dihydrate (1.26 g, 5.6 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction was then neutralized with aqueous sodium hydroxide solution. The organic layer was separated, washed with water, dried, and then concentrated to oil. The crude compound was purified by column chromatography over silica gel using ethyl acetate/pet ether (1:1) as eluent to give 1-methyl-2,3-dihydro-1H-indol-5-ylamine (0.12 g, 72%) as solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated to oil
  5. customThe crude compound was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-5515e6a14d3c4016a2ecc43e42f43aa8
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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