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

HRID 2163579Notes

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 eighteen 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-6068ada1928d4fe2b534e57efc1b9926
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04134981

Reaction notes

Loading…