Aluminium lithium hydride → 3-(Aminomethyl)-N-(2,4-dimethoxybenzyl)pyridin-2-amine

HRID 1695893Notes

Reaction equation

HRID 1695893 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:4]=1[CH2:5][NH:6][C:7]1[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][N:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[CH3:1][O:2][C:3]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:4]=1[CH2:5][NH:6][C:7]1[C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 222931752-(2,4-Dimethoxybenzylamino)nicotinonitrile

Product 1

HCID 222931603-(Aminomethyl)-N-(2,4-dimethoxybenzyl)pyridin-2-amine

Procedure

A solution of 2-(2,4-Dimethoxybenzylamino)pyridine-3-carbonitrile (0.55 g, 2.04 mmol) and LiAlH4 (2.2 ml of 1N, 4.4 mmol) was stirred at RT until the reaction was judged complete by LCMS. The reaction was quenched with sat. aq. Na2CO3 and the layers were separated. The organic layer was dried (Na2SO4) and the solvents removed under reduced pressure giving the desired product which was used without further purification. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=274; tR=0.28.

Workup

  1. customThe reaction was quenched with sat. aq. Na2CO3
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-a77032dec6524811947e135cdf50835b
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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