[CH3:1][CH:2]1[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[C:3]1O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH-].[Na+].CCOCC>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:3]2[CH:2]([CH3:1])[CH2:6][N:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]=2)=[CH:18][CH:17]=1A 100 ml round bottom flask was charged with 4-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-3-ol (1.00 g, 5.68 mmol), 4-methoxybenzenamine (2.27 g, 18.44 mmol), and p-toluenesulfonic acid monohydrate (0.59 g, 3.12 mmol). The reaction mixture was stirred at 140° C. under a nitrogen atmosphere for 16 h. The reaction was cooled and dissolved in 1% NaOH solution and ether. The organic layer was separated, washed with 1% HCl solution and water, then dried over Na2SO4, filtered, and concentrated to afford N-(4-methoxyphenyl)-4-methyl-1-phenyl-4,5-dihydro-1-H-pyrazol-3-amine as a brown solid. MS m/z=282.2 [M+H]+. Calc'd for C17H19N3O: 281.35.
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