Acetic Acid → 3-[(2,4-Dimethylphenyl)amino]-5-(dipropylamino)-1-methylpyridin-2(1H)-one

HRID 598057Notes

Reaction equation

HRID 598057 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11](=[O:20])[N:12]([CH3:19])[CH:13]=[C:14]([N+:16]([O-])=O)[CH:15]=1.[CH:21](=O)[CH2:22][CH3:23].[C:25](O)(=O)[CH3:26].[H][H].[CH2:31](O)C>[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11](=[O:20])[N:12]([CH3:19])[CH:13]=[C:14]([N:16]([CH2:31][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[CH:15]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 527PropanalHCID 702EthanolHCID 672679503-[(2,4-Dimethylphenyl)amino]-1-methyl-5-nitropyridin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 589385293-[(2,4-Dimethylphenyl)amino]-5-(dipropylamino)-1-methylpyridin-2(1H)-oneYield 3.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a mixture containing 0.11 g (0.40 mmol) of 3-[(2,4-dimethylphenyl)amino]-1-methyl-5-nitropyridin-2(1H)-one in 50 ml of ethanol was added 0.062 ml (0.86 mmol) of propionaldehyde, 0.15 ml of glacial acetic acid and 0.15 g of 10% palladium on carbon (Degussa type, 50% wet). The flask was fitted with a balloon of hydrogen and allowed to stir at room temperature for 4 h. The reaction was filtered through GF/F paper and the filtrate concentrated under reduced pressure. The residue was purified via preparative HPLC to afford 5 mg (3.7%) of product.

Workup

  1. filtrationThe reaction was filtered through GF/F paper
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-74d730e64c364b14af431f4ea9c68207
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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