[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Cl.[NH2:22][OH:23].N1C=CC=CC=1>CO.CCOCC>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]=[N:22][OH:23])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8]A mixture of 4-(3-fluoro-4-hydroxyphenyl)-naphthalene-1-carbaldehyde (570 mg, 2.13 mmol), hydroxylamine hydrochloride (297 mg, 4.27 mmol), and anhydrous pyridine (0.35 ml, 4.27 mmol) in MeOH (13 ml) was heated to reflux for 1.5 h. The mixture was then diluted with ether, washed with water, the organic layer was dried over anhydrous Na2SO4, passed through a silica plug and concentrated. Purification by reverse phase HPLC (water-CH3CN-0.1% TFA) afforded 400 mg (67%) of product as a white solid: mp 187–188° C.; 1H NMR (300 MHz, DMSO-d6): δ 7.12 (2H, m), 7.28 (1H, d, J=11.4 Hz), 7.45 (1H, d, J=7.4 Hz), 7.53–7.64 (2H, m). 7.83 (1H, d, J=7.5 Hz), 7.90 (1H, d, J=7.6), 8.73 (1H, d, J=8.1 Hz), 8.81 (1H, s), 10.08 (1H, s), 11.46 (1H, s); MS m/z 282 ([M+H]+).
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