HCID 21563494, compound → HCID 178482999, compound

HRID 1580622Notes

Reaction equation

HRID 1580622 reaction equation
[C:1]1([C:7]2[C:11]3[C:12](=[O:21])[C:13](=[O:20])[C:14]4[C:19]([C:10]=3[O:9][N:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[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:10](=[O:9])[C:19]2[C:14]([C:13](=[O:20])[C:12]=1[OH:21])=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 21563494HCID 21563494, compoundHCID 68133083HCID 68133083, compound

Product 1

HCID 178482999HCID 178482999, compound

Procedure

A solution of 3-phenyl-4,5-dihydronaphtho[2,1-d]-isoxazole-4,5-dione (500 mg) in 8 % 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 about 1.5 hours. After removal of the solvent, the residue is dissolved in methylene chloride, 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 (158 mg), which is identical with the product of Example 16.

Workup

  1. filtrationfilter at room temperature (20- 30°C) in argon atmosphere for about 1.5 hours
  2. customAfter removal of the solvent
  3. dissolutionthe residue is dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated
  7. washThe residue is washed with benzene

Sources & evidence

ORD record
ord-e01fcbd7cde846ec881b1623a05bad5b
Source dataset
uspto-grants-1976_01
Patent number
US03933828

Reaction notes

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