Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:9]([O-])=O.[Na+].[CH3:13][O:14][C:15]([CH2:17][C:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:19])=[O:16].[C:25]([O-:28])(=O)C.[Na+].[CH2:30]([OH:32])C>O>[CH3:24][O:23][C:21](=[O:22])[C:20](=[N:9][NH:2][C:3]1[CH:8]=[CH:7][C:6]([O:32][CH3:30])=[C:5]([O:28][CH3:25])[CH:4]=1)[C:18](=[O:19])[CH2:17][C:15]([O:14][CH3:13])=[O:16]A mixture of 2.5 ml of concentrated HCl, 5 ml of H2O, and 5.523 mmoles of aniline (26) was treated with a solution of sodium nitrite 381 mg (5.52 mmoles) in 5 ml of water in an ice bath. This reaction was stirred for two hours to give crude diazonium chloride (27) which was not isolated. The crude diazonium salt solution was poured into a mixture of 961 mg of dimethyl acetonedicarboxylate (2) in 3 ml of ethanol and 3 g of sodium acetate in 10 ml of water with vigorous stirring. Product precipitated immediately. The reaction was allowed to stir for an additional 2 hours, then filtered and dried to give 1.363 g of the desired hydrazone (28) as a solid. MS+: m/e=339.1 (M+H).
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