Water → (1h-indol-2-ylmethyl)amine

HRID 1601061Notes

Reaction equation

HRID 1601061 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)#[N:8].O>C1COCC1>[NH2:8][CH2:7][C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 962WaterHCID 37875991H-indole-2-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 582331(1h-indol-2-ylmethyl)amineYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (42 mL, 1M solution in THF) was added dropwise through a syringe to a solution of 2-cyanoindole (2.0 g, 14.1 mmol) in anhydrous THF (20 mL) with cooling, and the resulting solution was stirred at RT under argon for 5 h. H2O was added dropwise with cooling to destroy excess LAH, and the colorless precipitate was removed by filtration and washed with THF. The filtrate was dried (K2CO3) and concentrated to afford the title compound (2.11 g, quantitative) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 7.41 (d, 1H), 7.29 (d, 1H), 6.97 (t, 1H), 6.91 (t, 1H), 6.20 (s, 1H), 3.82 (s, 2H), 2. 18 (br, 1H).

Workup

  1. temperaturewith cooling
  2. temperaturewith cooling
  3. customto destroy excess LAH
  4. customthe colorless precipitate was removed by filtration
  5. washwashed with THF
  6. dry with materialThe filtrate was dried (K2CO3)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1c00970b2cd04f03bf78528a187e1121
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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