3-(2,4-Dimethylphenyl)-1-methyl-5-nitropyridin-2(1H)-one → 5-Amino-3-(2,4-dimethylphenyl)-1-methylpyridin-2(1H)-one

HRID 598054Notes

Reaction equation

HRID 598054 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:19])[N:11]([CH3:18])[CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1.[H][H]>C(O)C.[Pd]>[NH2:15][C:13]1[CH:14]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])[C:10](=[O:19])[N:11]([CH3:18])[CH:12]=1

Participants

5

Reactant 2

HCID 672674423-(2,4-Dimethylphenyl)-1-methyl-5-nitropyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672669435-Amino-3-(2,4-dimethylphenyl)-1-methylpyridin-2(1H)-oneYield 41.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution containing 0.17 g (0.66 mmol) of 3-(2,4-dimethylphenyl)-1-methyl-5-nitropyridin-2(1H)-one in 50 ml of ethanol was added 0.10 g of 10% palladium on carbon (Degussa type; 50% wet). The flask was fitted with a balloon of hydrogen and allowed to stir for 5 h. The reaction was filtered through GF/F paper and the filtrate concentrated under reduced pressure to afford 0.063 g (41.9%) of product.

Workup

  1. filtrationThe reaction was filtered through GF/F paper
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-0f2d926b1a3547e48f4d337bd28e9ca1
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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