[C:1](=[N:9][OH:10])([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16](N)=O.O>O1CCCC1.ClCCl>[C:2]1([C:1]2[N:8]=[C:16]([C:15]3[CH:14]=[CH:22][N:21]=[CH:20][CH:19]=3)[O:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
To a mixture of benzamide oxime (12.8 g, 94 mmol) and 4 Å sieves (80 g) in tetrahydrofuran (250 ml) under a nitrogen atmosphere was carefully added sodium hydride (55% dispersed in oil, 4.3 g, 98 mmol) portionwise. When addition was complete the reaction was heated at 50° C. for 1 hour. Methyl isonicotinamide (5.6 ml, 47 mmol) in tetrahydrofuran (50 ml) was added, and the reaction stirred at reflux for 2 hours. The reaction was cooled to room temperature and water (200 ml) and dichloromethane (300 ml) added. The mixture was filtered through a pad of Celite and the two phases separated. The aqueous phase was extracted with a further portion of dichloromethane (250 ml). The combined organic phases were washed with saturated brine (200 ml), dried (MgSO4) and evaporated in vacuo. The residue was triturated with ethyl acetate to yield the title compound as a white solid (2.64 g, 25%). δH (CDCl3) 7.50-7.56 (3H, m, ArH), 8.05-8.07 (2H, m, ArH), 8.16-8.19 (2H, m, ArH), 8.89 (2H, dd, J 4.4, 1.6 Hz, pyridyl 2-H, 6-H).
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