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

HRID 271901Notes

Reaction equation

HRID 271901 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:10]=1[CH2:11][NH:12][C:13]1[C:14]([C:19]#[N:20])=[N:15][CH:16]=[CH:17][CH:18]=1>O1CCCC1>[NH2:20][CH2:19][C:14]1[C:13]([NH:12][CH2:11][C:10]2[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:9]=2[O:8][CH3:7])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 222933003-(2,4-Dimethoxybenzylamino)picolinonitrile

Product 1

HCID 222932582-(Aminomethyl)-N-(2,4-dimethoxybenzyl)pyridin-3-amineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.0 M in THF, 13.3 mL, 13.3 mmol) was added slowly to a solution of 3-[(2,4-dimethoxybenzyl)amino]pyridine-2-carbonitrile (3.25 g, 12.1 mmol) in tetrahydrofuran (40 mL) at 0° C. The reaction was warmed to room temperature and stirred for 4 h. The reaction was carefully quenched with a saturated aqueous solution of sodium sulfate, filtered with copious dichloromethane and concentrated to produce the title compound (2.68 g). MS 274.3 (M+1).

Workup

  1. customThe reaction was carefully quenched with a saturated aqueous solution of sodium sulfate
  2. filtrationfiltered with copious dichloromethane
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-39e40efb745646f2922392f2a72635c4
Source dataset
uspto-grants-2008_11
Patent number
US07452903B2

Reaction notes

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