Anthranilic Acid → 1,4-Ethanonaphthalene, 1,4-dihydro-

HRID 10152

Reaction equation

HRID 10152 reaction equation
[C:1](O)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)N.[CH:11]1[CH2:16]CC=[CH:13][CH:12]=1.N(O[CH2:20]CC(C)C)=O>O1CCCC1>[CH:2]12[CH2:8][CH2:7][CH:6]([C:5]3[C:3]1=[CH:13][CH:12]=[CH:11][CH:16]=3)[CH:20]=[CH:1]2

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 8053Isoamyl NitriteHCID 116051,3-Cyclohexadiene

Product 1

HCID 1389941,4-Ethanonaphthalene, 1,4-dihydro-Yield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution of 1 g (7.3 mmol) of anthranilic acid was dropped into a mixed solution under reflux of 0.77 ml (8.0 mmol) of 1,3-cyclohexadiene, 1.1 ml of isoamyl nitrite and 50 ml of tetrahydrofuran. Then, the resultant solution was heated and refluxed for 2 hours to remove THF, extracted with chloroform, washed with distilled water and saturated saline, dried with anhydrous sodium sulfate and purified with silica gel column-chromatography-(chloroform) to obtain 1,4-dihydro-1,4-ethanonaphthalene (0.89 g, 5.7 mmol, yield: 78%).

Workup

  1. temperaturerefluxed for 2 hours
  2. customto remove THF
  3. extractionextracted with chloroform
  4. washwashed with distilled water and saturated saline
  5. dry with materialdried with anhydrous sodium sulfate
  6. custompurified with silica gel column-chromatography-(chloroform)

Sources & evidence

ORD record
ord-a17440283c1b4d1dba9b75e78b2c71b4
Source dataset
uspto-grants-2006_08
Patent number
US07094625B2

Linked notes

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