Anthranilic Acid → 1,4-Dihydro-1,4-epoxynaphthalene

HRID 262424Notes

Reaction equation

HRID 262424 reaction equation
N(O[CH2:4][CH2:5][CH:6](C)C)=O.[C:9]([OH:18])(=O)[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)N.O1C=CC=C1.[OH-].[Na+]>C(COC)OC>[CH:15]1[CH:16]=[C:10]2[C:11]([CH:6]3[O:18][CH:9]2[CH:4]=[CH:5]3)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 8029FuranHCID 8053Isoamyl NitriteHCID 14798Sodium Hydroxide

Product 1

HCID 971391,4-Dihydro-1,4-epoxynaphthaleneYield 51%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

Solutions of 20 ml of isoamyl nitrite in glyme (20 ml) and of 13.7 g of anthranilic acid in glyme (45 ml) were added simultaneously by drops to a refluxing mixture of glyme (50 ml) and furan (50 ml). Refluxing was continued for ten minutes and the brown solution was cooled, made basic with aqueous sodium hydroxide (1 N), and extracted with petroleum ether. The extract was washed thoroughly with water, clarified with Norit®, dried, and evaporated to give an oil. The oil solidified on cooling to give 7 g (51% yield) of light yellow solid. Recrystalization of the yellow solid from petroleum ether gave colorless crystalline solid of 1,4-dihydronaphthalene-1,4-endo-oxide (IIIa), m.p. 53°-54° C. (lit. m. p. 56° C.).

Workup

  1. temperatureRefluxing
  2. waitwas continued for ten minutes
  3. temperaturethe brown solution was cooled
  4. extractionextracted with petroleum ether
  5. washThe extract was washed thoroughly with water
  6. customdried
  7. customevaporated
  8. customto give an oil
  9. temperatureon cooling
  10. customto give 7 g (51% yield) of light yellow solid
  11. customRecrystalization of the yellow solid from petroleum ether

Sources & evidence

ORD record
ord-159310a41f7b4ea982f78273c7f695f8
Source dataset
uspto-grants-1979_05
Patent number
US04154745

Reaction notes

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