Sodium Hydroxide → (1H-indol-4-yl)methanamine

HRID 393006

Reaction equation

HRID 393006 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]#[N:17])[C:10]=2[CH:9]=[CH:8]1.[OH-].[Na+]>O1CCCC1>[NH:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:16][NH2:17])[C:10]=2[CH:9]=[CH:8]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 38176024-CyanoindoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 280302(1H-indol-4-yl)methanamineYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (3.80 g, 100.0 mmol) was added in 0.5 g portions over 30 min to a solution of 1H-indole-4-carbonitrile (prepared according to Clark, Robin D.; Repke, David B. J. Heterocycl. Chem. 1985, 22, 121-5; 7.50 g, 52.8 mmol) in tetrahydrofuran (250 mL). The mixture was heated at reflux for 30 min. A solution of 1 M sodium hydroxide was added to quench excess lithium aluminum hydride. The mixture was filtered and the filter cake was washed with water. The filtrate was first made acidic with 1 N HCl and then made basic again by the addition of saturated aqueous NaHCO3. The water layer was then extracted with nBuOH. Evaporation of nBuOH, and drying under vacuum gave 1H-indole-4-methanamine (6.24 g, 80%) as a beige solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 min
  3. customto quench excess lithium aluminum hydride
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with water
  6. additionmade basic again by the addition of saturated aqueous NaHCO3
  7. extractionThe water layer was then extracted with nBuOH
  8. customEvaporation of nBuOH
  9. customdrying under vacuum

Sources & evidence

ORD record
ord-d91ce68bf8464e15b7cf6436b971fcec
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Linked notes

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