[OH:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.Cl.[N:13]([O-])=O.[Na+].[CH3:17][CH:18](C(C)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20].[OH-].[K+]>O.C(O)C.C(#N)C>[OH:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][N:13]=[C:18]([CH3:17])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1
To a mixture of 4-hydroxy-2-nitroaniline (5.0 g), 1N hydrochloric acid (65 mL) and acetonitrile (20 mL) was added dropwise an aqueous solution (10 mL) of sodium nitrite (2.44 g) at 0-5° C., and the reaction mixture was stirred at 0° C. for 10 min. This mixture was added dropwise to a mixture of ethyl 2-methylacetoacetate (5.61 g), 85% potassium hydroxide (4.37 g), ethanol (50 mL) and water (50 mL) at 0-5° C. After the completion of the dropwise addition, 1N hydrochloric acid (13 mL) and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried (MgSO4), and concentrated. The obtained residue was washed with hexane to give the title compound (4.94 g, yield 57%) as brown crystals.
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