2-((1H-Indol-4-yl)oxy)acetonitrile → 2-(1H-indol-4-yloxy)ethan-1-amine

HRID 1872838Notes

Reaction equation

HRID 1872838 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][C:12]#[N:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[NH:1]1[C:9]2[C:4](=[C:5]([O:10][CH2:11][CH2:12][NH2:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 155417992-((1H-Indol-4-yl)oxy)acetonitrileHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 154812802-(1H-indol-4-yloxy)ethan-1-amineYield 33%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-(1H-indol-4-yloxy)-acetonitrile (0.9 g, 5.2 mmol) in anhydrous ethyl ether (30 ml) was added lithium aluminum hydride (95%, 0.21 g, 5.2 mmol) at room temperature. The reaction was allowed to reflux for 2 hours, another equivalent of lithium aluminum hydride (0.21 g, 5.2 mmol) was added. The reaction was allowed to reflux for another 2 hours and then was quenched with 1N sodium hydroxide and water. The solid was removed by filtration and the filtrate was concentrated and dissolved in methanol and water. To a above mixture was added 2N hydrochloric acid until pH<3 and then extracted with ethyl ether. To the above aqueous layer was added sodium hydroxide until pH>9, the mixture was extracted with isopropanol-methylene (1:3). The combined organic layers were washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under vacuum to afford 0.3 g (33%) of product as a brown solid. mp: 123-125° C.; MS EI m/e 177 (M+)

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureto reflux for another 2 hours
  3. customwas quenched with 1N sodium hydroxide and water
  4. customThe solid was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. dissolutiondissolved in methanol
  7. additionTo a above mixture was added 2N hydrochloric acid until pH<3
  8. extractionextracted with ethyl ether
  9. additionTo the above aqueous layer was added sodium hydroxide until pH>9
  10. extractionthe mixture was extracted with isopropanol-methylene (1:3)
  11. washThe combined organic layers were washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-4172a2b8a7d94d419c4e71cca117206a
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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