3-Phenylnaphtho[2,3-d][1,2]oxazole-4,9-dione → HCID 178510514, compound

HRID 1580619Notes

Reaction equation

HRID 1580619 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>C(O)C.[Ni]>[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)(=[NH:8])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 151852683-Phenylnaphtho[2,3-d][1,2]oxazole-4,9-dione

Product 1

HCID 178510514HCID 178510514, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 3-phenyl-4,9-dihydronaphtho-[2,3-d]isoxazole-4,9-dione (m.p. 133°-135°C, 2.0 g) in ethanol (200 ml) is added Raney nickel prepared from 50 % Raney-Nickel alloy (3 g). The mixture is subjected to catalytic reduction procedure at room temperature (20°-30°C) under atmospheric pressure. After completion of hydrogen absorption, the catalyst is removed by filtration and the ethanol is evaporated. The residue is chromatographed on alumina and eluted with methylenechloride-methanol (95:5). The yellowish crystals obtained are washed with ether-ethyl acetate and recrystallized from 80 % acetic acid to give 2-benzimidoyl-3-hydroxy-1,4-naphthoquinone (1.01 g) as pale yellow scales, m.p. 258°-259°C, which is identical with the product of the part [A] above.

Workup

  1. customis subjected to catalytic reduction procedure at room temperature
  2. custom(20°-30°C)
  3. customAfter completion of hydrogen absorption
  4. customthe catalyst is removed by filtration
  5. customthe ethanol is evaporated
  6. customThe residue is chromatographed on alumina
  7. washeluted with methylenechloride-methanol (95:5)
  8. customThe yellowish crystals obtained
  9. washare washed with ether-ethyl acetate
  10. customrecrystallized from 80 % acetic acid

Sources & evidence

ORD record
ord-222c52244d4a4847b23cca35b891cdb1
Source dataset
uspto-grants-1976_01
Patent number
US03933828

Reaction notes

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