Diethyl Oxalate → Ethyl 7-fluoropyrimido[4,5-b]quinolin-4(3H)-one-2-carboxylate

HRID 442204Notes

Reaction equation

[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([NH2:22])[C:16]([C:23]([NH2:25])=[O:24])=[CH:15]2>CCCCCC>[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]1[N:22]=[C:2]([C:1]([O:8][CH2:9][CH3:10])=[O:7])[NH:25][C:23](=[O:24])[C:16]1=[CH:15]2

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of diethyl oxalate (57.2 g., 0.392 mole) and 6-fluoro-2-aminoquinoline-3-carboxamide (5.34 g., 0.0261 mole) is heated for 18 hours at 160° C. under a nitrogen atmosphere and then allowed to cool to room temperature. Hexane (300 ml.) is added, the mixture stirred and filtered to provide the desired product. It is washed with hexane and dried. Yield = 4.9 g (71%); m.p. 272° C. (dec.).

Workup

temperatureto cool to room temperature
filtrationfiltered

Sources & evidence

ORD record: ord-5d81a5c632f04d3b856c06ea079168d9
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04044134

Reaction notes

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