CO.[CH3:3][O:4][C:5]([C:7]1[C:12](=[O:13])[CH:11]=[C:10]([CH3:14])O[C:8]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:6].[CH2:22]([NH2:24])[CH3:23].Cl>O.C(O)(=O)C>[CH2:22]([N:24]1[C:10]([CH3:14])=[CH:11][C:12](=[O:13])[C:7]([C:5]([O:4][CH3:3])=[O:6])=[C:8]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH3:23]A 1000 ml flask is fitted with a magnetic stirring bar and a sidearm addition funnel. 500 mls of methanol, 30 mls of glacial acetic acid and 60 gms of 3-methoxycarbonyl-6-methyl-2-(4'-chlorophenyl)-4-pyrone are added. 120 mls of 70% aqueous ethylamine is placed in the addition funnel and added very slowly (4 hr. addition time). 50 mls of water is then added followed by 100 mls of concentrated HCl (cooling required). The reaction mixture is allowed to stand undisturbed for 30 minutes. The bulk of the methanol is then removed in vacuo leaving 46.1 gms of methyl 1-ethyl-6-methyl-2-(4'-chlorophenyl)-4-oxonicotinate. mp (methylene chloride/ether)=217°-219° C.
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