Acetic Acid → 4,6-Dimethyl-3-nitropyridin-2(1H)-one

HRID 2077629Notes

Reaction equation

HRID 2077629 reaction equation
[N+:1]([CH2:4][C:5]([O:7]CC)=O)([O-:3])=[O:2].[CH3:10][C:11](=O)[CH2:12][C:13](=O)[CH3:14].[N:17]1C=CC=CC=1.C(O)(=O)C>[OH-].[NH4+]>[CH3:10][C:11]1[CH:12]=[C:13]([CH3:14])[NH:17][C:5](=[O:7])[C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 31261AcetylacetoneHCID 69379Ethyl nitroacetate

Product 1

HCID 5359724,6-Dimethyl-3-nitropyridin-2(1H)-oneYield 104.1%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of ethyl nitroacetate (80.0 g, 601 mmol) in ammonium hydroxide (25% NH3 in water, 400 mL) was stirred at room temperature for 3 days, and then the solution was concentrated by air-drying. The residue was dissolved in water (450 mL). To the solution was added 2,4-pentanedione (73.1 g, 730 mmol), pyridine (16.2 mL, 200 mmol) and acetic acid (11.4 mL, 200 mmol), and the mixture was stirred for an additional 7 days. The resulting precipitates were collected by filtration and dried under reduced pressure to give 35.0 g (35%) of the title compound as yellow solids: 1H-NMR (DMSO-d6) δ 12.44 (1H, br.s), 6.06 (1H, s), 2.19 (3H, s), 2.13 (3H, s).

Workup

  1. concentrationthe solution was concentrated
  2. customby air-drying
  3. dissolutionThe residue was dissolved in water (450 mL)
  4. stirringthe mixture was stirred for an additional 7 days
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-68dd7996428640c6b31d4f6d7114319f
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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