3-Phenylnaphtho[2,3-d][1,2]oxazole-4,9-dione → HCID 178482999, compound

HRID 1580621Notes

Reaction equation

HRID 1580621 reaction equation
[C:1]1([C:7]2[C:11]3[C:12](=[O:21])[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:19](=[O:20])[C:10]=3[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22]NC.O1CCOCC1>>[CH3:22][N:8]=[C:7]([C:11]1[C:12](=[O:21])[C:13]2[C:18]([C:19](=[O:20])[C:10]=1[OH:9])=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 151852683-Phenylnaphtho[2,3-d][1,2]oxazole-4,9-dioneHCID 68133083HCID 68133083, compound

Product 1

HCID 178482999HCID 178482999, compound

Procedure

A solution of 3-phenyl-4,9-dihydronaphtho[2,3-d]-isoxazole-4,9-dione (1.0 g) in 6.6 % dimethylamine-dioxane solution (100 ml) is irradiated by light of a high-pressure mercury lamp (1 KW) through a pyrex filter at room temperature (20°-30°C) in argon atmosphere for 3.3 hours. After removal of the solvent, the residue is dissolved in methylene chloride. The solution is washed with water, dried with anhydrous sodium sulfate, and evaporated. The residue is washed with benzene to give 2-(N-methylbenzimidoyl)-3-hydroxy-1,4-naphthoquinone (252 mg). Recrystallization from methanol gives yellow prisms, m.p. 235°-237°C.

Workup

  1. filtrationfilter at room temperature (20°-30°C) in argon atmosphere for 3.3 hours
  2. customAfter removal of the solvent
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washThe solution is washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated
  7. washThe residue is washed with benzene

Sources & evidence

ORD record
ord-22fcb462a1aa46c4bac091f39d566734
Source dataset
uspto-grants-1976_01
Patent number
US03933828

Reaction notes

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