[CH:1]1[C:6]2[CH2:7][CH:8]3[C:13](=O)[CH:11]([CH2:12][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH2:10][CH2:9]3.Cl.[NH2:16][OH:17]>N1C=CC=CC=1.CCO>[CH:1]1[C:6]2[CH2:7][CH:8]3[C:13](=[N:16][OH:17])[CH:11]([CH2:12][C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH2:10][CH2:9]3To a solution of 34.3 g of 5,6,7,8,9,10-hexahydro-6,9-methano-benzo[a][8]annulen-11-one (0.184 mol) in 100 mL of pyridine and 100 mL of EtOH was added 29.7 g of hydroxylamine hydrochloride (0.460 mol). The resultant solution was refluxed for 4 hours prior to concentration in vacuo. The residue was partitioned between CH2Cl2 and 10% aqueous citric acid. The aqueous layer was extracted with CH2Cl2 (4×200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the oxime.
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