[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N:10]([O-])=O.[Na+].[CH2:14]([O:16][C:17](=[O:23])[CH2:18]C(CCl)=O)[CH3:15].C([O-])(=O)C.[Na+].[ClH:29]>O.C(O)C>[Cl:29]/[C:18](=[N:10]\[NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)/[C:17]([O:16][CH2:14][CH3:15])=[O:23]
To p-anisidine (16 g, 0.129 mol) in conc. HCl (40 mL) and 100 mL H2O, cooled to −5° C., was added sodium nitrite (9.4 g, 0.136 mol) in H2O (60 mL). The reaction mixture was stirred at −5° C. for 20 min and a mixture of ethylchloroacetoacetate (22 g, 0.133 mol), ethanol (100 mL), sodiumacetate (32 g, 0.389 mmol), and H2O (400 mL) was added. The reaction was allowed to warm up to room temperature and stirred for 2 h. The product precipitated as a black solid. It was filtered and dried (30 g). 1H NMR (CDCl3) δ: 8.28 (s, 1H), 7.18 (d, 2H), 6.90 (d, 2H), 4.41 (q, 2H), 3.80 (s, 3H), 1.42 (t, 3H) ppm.
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