3-Methoxybenzonitrile → 3-Methoxybenzylamine

HRID 911271Notes

Reaction equation

HRID 911271 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13]>C(OCC)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][NH2:13]

Participants

4

Reactant 2

HCID 737123-MethoxybenzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 211563-MethoxybenzylamineYield 93.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add lithium aluminum hydride (3.795 g, 100 mmol) portion wise to a solution of 3-methoxybenzonitrile (5.326 g, 40 mmol) in anhydrous ethyl ether (200 mL) at 0° C. Stir for 1 h, warm to ambient temperature and continue to stir for 12 h. Quench the reaction with 0.1N aqueous NaOH, filter the solid, dry the filtrate over Na2SO4 and concentrate to give the title compound as a colorless oil (5.107 g, 93%). MS (ES+) m/z: 138 (M+H)+.

Workup

  1. stirringto stir for 12 h
  2. customQuench
  3. customthe reaction with 0.1N aqueous NaOH
  4. filtrationfilter the solid
  5. dry with materialdry the filtrate over Na2SO4
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-9d293b9e1d3c4e0ab8286adb57ace228
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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