Anthranilic Acid → 1,4-Ethanonaphthalene, 1,4-dihydro-
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]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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%).