C[O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:14]([CH3:15])=[CH:13][N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:11]=2)=[CH:5][CH:4]=1.Br.C(O)(=O)C.[OH-].[Na+]>O>[CH3:15][C:14]1[C:10]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)=[N:11][N:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:13]=1A 50 ml round bottom flask was charged with N-(4-methoxyphenyl)-4-methyl-1-phenyl-1H-pyrazol-3-amine (0.37 g, 1.33 mmol), hydrobromic acid (2.16 ml, 39.74 mmol), and acetic acid (2.27 ml, 39.74 mmol). The reaction mixture was stirred at 110° C. for 4 h, then cooled to RT and diluted with water. The solution was neutralized with 6 N NaOH until a pH of about 6, upon which the product precipitated out of solution. The solid was filtered and dried under high vacuum to afford 4-(4-methyl-1-phenyl-1H-pyrazol-3-ylamino)phenol as a dark solid. MS m/z=266.1 [M+H]+. Calc'd for C16H15N3O: 265.31.
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