2-Nitroacetamide → 2(1H)-Pyridinone, 5-ethyl-6-methyl-3-nitro-

HRID 1589783Notes

Reaction equation

HRID 1589783 reaction equation
[CH2:1]([CH:3]([C:6](=O)[CH3:7])[CH:4]=O)[CH3:2].[Na].[N+:10]([CH2:13][C:14]([NH2:16])=[O:15])([O-:12])=[O:11].C([O-])(=O)C.[NH2+]1CCCCC1>O>[CH2:6]([C:3]1[CH:4]=[C:13]([N+:10]([O-:12])=[O:11])[C:14](=[O:15])[NH:16][C:1]=1[CH3:2])[CH3:7]

Participants

6

Reactant 4

HCID 2792562-NitroacetamideHCID 3014295Piperidinium acetateHCID 5360545SodiumHCID 152284102-Ethyl-3-oxobutanal

Product 1

HCID 103523142(1H)-Pyridinone, 5-ethyl-6-methyl-3-nitro-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-ethyl-3-oxobutanal, sodium salt (7.5 g, 55 mmol), nitroacetamide (6.6 g, 63 mmol), aqueous piperidinium acetate (4.4 mL) [prepared from glacial acetic acid (42 mL), water (100 mL) and piperidine (72 mL)] in water (45 mL) was stirred at room temperature for 22 hours. The yellow precipitate was collected by filtration and air dried to yield 8.0 g (80%) of 5-ethyl-6-methyl-3-nitro-2-(1H)-pyidinone.

Workup

  1. filtrationThe yellow precipitate was collected by filtration and air
  2. customdried
  3. customto yield 8.0 g (80%) of 5-ethyl-6-methyl-3-nitro-2-(1H)-pyidinone

Sources & evidence

ORD record
ord-18a5715270204d3ab0551f735bd934a3
Source dataset
uspto-grants-1993_04
Patent number
US05200329

Reaction notes

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