4-(Dimethylamino)benzonitrile → 4-(Aminomethyl)-N,N-dimethylaniline

HRID 1505163Notes

Reaction equation

HRID 1505163 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[NH2:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([N:2]([CH3:11])[CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 709674-(Dimethylamino)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 808264-(Aminomethyl)-N,N-dimethylanilineYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Commercially available 4-dimethylaminobenzonitrile 18i (2 g, 13.7 mmol) dissolved in 15 ml of ether was added dropwise at 0° C. to LiAlH4 (2 equiv., 1 g) suspended in diethyl ether (40 ml). The mixture was stirred at room temperature for 24 hours. The reaction was quenched by addition of water and filtrated and the salts were washed with ether. The organic phase was separated, anhydrified and evaporated giving 1.85 g of a pale yellow oil. Yield=90% 1HNMR (DMSO, 200 MHz) δ 1.60 (2H, bs), 2.84 (6H, s), 3.57 (2H, s), 6.67 (2H, d, J=8.8 Hz), 7.12 (2H, d, J=8.6 Hz)

Workup

  1. customThe reaction was quenched by addition of water
  2. filtrationfiltrated
  3. washthe salts were washed with ether
  4. customThe organic phase was separated
  5. customevaporated

Sources & evidence

ORD record
ord-6fd51c05e6684a879c368a16e1cfc526
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

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