Hexane → Ethyl 6-methoxy-7-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate

HRID 228863Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]=[C:11]([C:17]([O:19]CC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][C:4]=1[CH3:22].CCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][C:4]=1[CH3:22])[NH:9][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]2=[O:19]

Participants

Conditions

Temperature: 220 °C

Procedure

Diethyl 2-[(4-methoxy-3-methyl-phenylamino)-methylene]-malonate (73.9 g) was dissolved in diphenyl ether (200 ml) to prepare a solution which was then stirred at 220° C. for 2 hr. The reaction solution was cooled to room temperature, hexane was then added to the reaction solution, and the precipitated crystal was collected by filtration to give ethyl 6-methoxy-7-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate (25.5 g, yield 35%).

Workup

customto prepare a solution which
temperatureThe reaction solution was cooled to room temperature
filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record: ord-d9fe981624304f4497da73d8ac106824
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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