Aluminium lithium hydride → HCID 22124972, compound

HRID 1858327Notes

Reaction equation

HRID 1858327 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([CH2:13][CH3:14])([CH2:11][CH3:12])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:10][CH2:9][C:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH2:1])([CH2:11][CH3:12])[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22125118HCID 22125118, compound

Product 1

HCID 22124972HCID 22124972, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.5 g (13 mmol) of 2-(3-amino-phenyl)-2-ethyl-butyronitrile in 30 ml of tetrahydrofuran was treated with 30 ml (30 mmol) of a 1M solution of lithium aluminium hydride in tetrahydrofuran and the mixture was heated at reflux for 2 hours then cooled. The mixture was cautiously quenched by the addition of 1 ml water, 0.5 ml 2M sodium hydroxide and 1.5 ml water and then filtered through hyflo filter aid. The filtrate was evaporated to give 0.88 g (35%) of 3-(1-aminomethyl-1-ethyl-propyl)-aniline as a pale yellow oil. [Mass spectrum (ESI) MH+ =193].

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturethen cooled
  4. customThe mixture was cautiously quenched by the addition of 1 ml water, 0.5 ml 2M sodium hydroxide and 1.5 ml water
  5. filtrationfiltered through hyflo
  6. filtrationfilter aid
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-714f2c0323b34bfba9f47a6f04c4873a
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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