Water → 3-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one

HRID 1500970Notes

Reaction equation

HRID 1500970 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[C:10]#[N:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:11][CH2:10][C:3]1[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 698563-Cyano-4,6-dimethyl-2-hydroxypyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (500 mg, 3.4 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (258 mg, 6.8 mmol) at 0° C. The mixture was stirred at 20° C. for 2 hours. Then water (1 mL) was added and the product 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one was obtained as a white solid (300 mg, 60%). 1H NMR (300 MHz, d6-DMSO): δ 11.84 (s, 1H), 7.95 (s, 2H), 5.97 (s, 1H), 3.77 (s, 2H), 2.19 (s, 3H), 2.15 (s, 3H).

Sources & evidence

ORD record
ord-52542309de384db49d8e6ee7348b142c
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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