Benzoylacetone → Methanone, (3-methyl-1,4-dioxido-2-quinoxalinyl)phenyl-

HRID 1439514Notes

Reaction equation

HRID 1439514 reaction equation
[N+:1]1([O-:10])[O:5][N:4]=[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=12.[C:11]([CH2:19][C:20](=O)[CH3:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>C(O)C>[C:11]([C:19]1[C:20]([CH3:21])=[N+:4]([O-:5])[C:3]2[C:2](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N+:1]=1[O-:10])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7166BenzoylacetoneHCID 14798Sodium HydroxideHCID 68075Benzofuroxan

Product 1

HCID 178428812Methanone, (3-methyl-1,4-dioxido-2-quinoxalinyl)phenyl-Yield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 80 g. (0.59 mol.) of benzofurazan 1-oxide and 95 g. (0.59 mol.) of benzoylacetone in 1,000 ml. of ethanol was added 1.6 g. (0.04 mol.) of finely divided sodium hydroxide. The mixture became clear after about 30 minutes. Stirring was continued for a further 16 hours, and then the solid which had precipitated was collected by filtration. It was washed with ethanol, and dried to afford 153 g. (92% yield) of 2-benzoyl-3-methylquinoxaline 1,4-dioxide, m.p. 229°-231° C.

Workup

  1. additionTo a stirred suspension of 80 g
  2. waitwas continued for a further 16 hours
  3. customthe solid which had precipitated
  4. filtrationwas collected by filtration
  5. washIt was washed with ethanol
  6. customdried
  7. customto afford 153 g

Sources & evidence

ORD record
ord-f97e5f94fc2441039a8879f471ad8edc
Source dataset
uspto-grants-1977_11
Patent number
US04060523

Reaction notes

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