N[CH2:2][C:3]1([OH:15])[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.N([O-])=O.[Na+]>O1CCOCC1.C(O)(=O)C.O.C(OCC)(=O)C>[CH3:14][O:13][C:8]1[C:7]2[CH2:6][CH2:5][CH2:4][C:3](=[O:15])[CH2:2][C:12]=2[CH:11]=[CH:10][CH:9]=1To a solution of 1-aminomethyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-ol (26.6 g) in 1,4-dioxane (60 ml), acetic acid (24 ml) and water (210 ml) was added sodium nitrite (9.7 g) in water (60 ml) dropwise at 5° C., and the mixture was stirred at the same temperature for 2.5 hours. The resulting mixture was diluted with ethyl acetate and separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford 1-methoxy-5,7,8,9-tetrahydro-6H-benzocyclohepten-6-one (12.7 g).
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