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

HRID 1112244Notes

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-fb6dfee72ed44c1dad046f78345988da
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04120962

Reaction notes

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