[C:1]([C:3]1[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1)#[N:2].C1(C)C=CC=CC=1.S(=O)(=O)(O)[OH:30].[OH-].[Na+]>O>[CH3:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:4]1[CH:5]=[C:6]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[N:7]=[CH:8][C:3]=1[C:1]([NH2:2])=[O:30]A mixture of 5-cyano-4-(2-methylphenyl)-2-(4-morpholinyl)pyridine (17.71 g), 18 mL of toluene, and 17.0 mL (33.1 g, 319 mmol) of concentrated sulfuric acid was heated at 70° C. for 12 hours, cooled to room temperature, and quenched by addition of 100 mL of cold H2O. Ethyl acetate (100 mL) was added followed by a solution of 25.5 g (638 mmol) of sodium hydroxide in 50 mL of H2O. The aqueous layer was separated and extracted three times with 50 mL of ethyl acetate. The organic layers were combined and concentrated to afford 19.14 g of 4-(2-methylphenyl)-6-(4-morpholinyl)-3-pyridinecarboxamide as a colorless solid (LC assay 87.7 wt %) (yield 94.9–97%).
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