Water → (1H-indol-5-yl)methanamine

HRID 980288Notes

Reaction equation

HRID 980288 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27513Indole-5-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 54791(1H-indol-5-yl)methanamineYield 86.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1H-indole-5-carbonitrile (3.7 g) in tetrahydrofuran (25 ml) was added over fifteen minutes to a stirred suspension of lithium aluminium hydride (3.1 g) in tetrahydrofuran (80 ml) under nitrogen. After thirty minutes, the suspension was heated at reflux for two hours. After cooling to 0°, water (3.1 ml), sodium hydroxide (2N, 6.2 ml) and water (9.3 ml) were added with caution, the resulting salts were filtered off and the filtrate was concentrated under vacuum to afford a yellow oil (3.3 g) which was crystallised from ethyl acetate to give the title compound as a pale cream solid m.p. 114°-5°.

Workup

  1. waitAfter thirty minutes
  2. temperaturethe suspension was heated
  3. temperatureat reflux for two hours
  4. temperatureAfter cooling to 0°
  5. filtrationthe resulting salts were filtered off
  6. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3f99a3087b77427bbc343c457a4895b8
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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