[C:1]1(=[O:7])[O:6][CH:4]([CH3:5])[CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[N:27]=[CH:26][CH:25]=[CH:24][C:18]=2[C:19](OCC)=[O:20])[CH:12]=[CH:13][C:14]=1[Cl:15].CC(C)([O-])C.[K+].[OH-].[K+]>>[Cl:8][C:9]1[CH:10]=[C:11]([N:16]2[C:17]3[C:18](=[CH:24][CH:25]=[CH:26][N:27]=3)[C:19]([OH:20])=[C:2]([CH2:3][CH:4]([OH:6])[CH3:5])[C:1]2=[O:7])[CH:12]=[CH:13][C:14]=1[Cl:15]A stirred mixture of gamma-valerolactone (40 g.), ethyl 2-(3,4-dichlorophenylamino)-nicotinate (20 g.) and potassium t-butoxide (30 g.) was warmed in an atmosphere of nitrogen to 110° C. and kept there for 5 hr. After cooling somewhat the product was poured into 1000 ml. of 5% KOH solution and was allowed to stir overnight. The basic solution was extracted with ether (2×500 ml.) and the aqueous solution was acidified to pH 5 with conc. HCl. The solid was filtered off, washed with water, dried in air then recrystallized from methanol/charcoal to yield the desired product, m.p. 232°-234° C.
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