HCID 21563494, compound → HCID 178510514, compound

HRID 1580620Notes

Reaction equation

HRID 1580620 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>CO>[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)(=[NH:8])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 21563494HCID 21563494, compound

Product 1

HCID 178510514HCID 178510514, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-phenyl-4,5-dihydronaphtho-[2,1-d]isoxazole-4,5-dione (40 mg) in methanol (40 ml) is irradiated by light of a high-pressure mercury lamp (1 KW) at room temperature (20°-30°C) for about 1 hour. After removal of the solvent, the residue is chromatographed on alumina and eluted with methylene chloride-methanol (20:1). The eluate is evaporated and the residue is washed with isopropyl ether-ether to give 2-benzimidoyl-3-hydroxy-1,4-naphthoquinone (23 mg). Recrystallization from acetic acid gives pale yellow scales, m.p. 258°-259°C, identical with the product of Example 1.

Workup

  1. customAfter removal of the solvent
  2. customthe residue is chromatographed on alumina
  3. washeluted with methylene chloride-methanol (20:1)
  4. customThe eluate is evaporated
  5. washthe residue is washed with isopropyl ether-ether

Sources & evidence

ORD record
ord-adfc02b87e3e49059f3fc2dd1ac27f40
Source dataset
uspto-grants-1976_01
Patent number
US03933828

Reaction notes

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