[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].Cl.[N:13]([O-])=O.[Na+].[CH3:17][C:18]1[NH:19][N:20]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:21](=[O:23])[CH:22]=1.C(=O)([O-])O.[Na+]>O.C(O)C>[OH:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[N:1]=[N:13][C:22]1[C:18]([CH3:17])=[N:19][N:20]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:21]=1[OH:23])[C:6]([OH:8])=[O:7]
A solution of 4-amino-3-hydroxybenzoic acid (0.77 g, 0.005 mol.) in 1N aqu. hydrochloric acid (15.0 mL) was cooled to 0° C. and treated slowly with a solution of sodium nitrite (0.38 g; 0.0055 mol.) in water (5.0 mL). After addition the solution was stirred at 0° C. for 10 min. then 3-methyl-1-(4-methylphenyl)-3-pyrazolin-5-one (0.94 g; 0.005 mol.) was added in one portion. Ethanol (15.0 mL) was added followed by sat. aqu. sodium hydrogen carbonate until the pH of the solution was 8 (ca. 10 mL needed). The red solution was then stirred at room temperature for 16 h.
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