[H-].[Na+].O=[C:4]1[C:9]2[CH:10]=[CH:11]C=CC=2O[NH:6][C:5]1=O.[CH2:15]([N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24](C3C=NC=CC=3)[CH:25]=2)[C:20](=[O:33])[C:19]([C:34]([OH:36])=[O:35])=[CH:18]1)[CH3:16].[CH2:37](Br)[CH3:38].C(OCC)(=O)CC(OCC)=[O:43]>CN(C=O)C.C(O)(=O)C>[CH2:15]([N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:9]3[CH:4]=[CH:5][N:6]=[CH:11][CH:10]=3)[CH:25]=2)[C:20](=[O:33])[C:19]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:18]1[OH:43])[CH3:16]To a suspension of 0.53 g sodium hydride (50%) in 50 ml DMF was added 2.40 g dioxobenzoxazine from part (a). After 15 min. 1.20 g ethyl bromide was added and the mixture was stirred overnight at room temperature. Sodium hydride (1.06 g) was then added followed by 3.52 g diethyl malonate dropwise. The reaction mixture was heated on a steam bath for 2 hrs., then poured into dilute acetic acid and concentrated in vacuo. The residue was chromatographed on silica gel to give 1.35 g ethyl 1-ethyl-1,4-dihydro-2-hydroxy-4-oxo-7-(4-pyridinyl)-3quinolinecarboxylate used directly in the next reaction. A sample of the compound upon further purification was obtained as a yellow powder, m.p. 153-157° C.
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