Ethanol → N-(2,4-dimethoxybenzyl)-N-phenyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide

HRID 1852416Notes

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[C:14]([O:16]CC)=O.[CH3:19][O:20][C:21]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:22]=1[CH2:23][NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.N#N.CCO>CCCCCCC>[CH3:19][O:20][C:21]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:22]=1[CH2:23][N:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:14]([C:3]1[C:4](=[O:13])[N:5]([CH3:12])[C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:16]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of ethyl 1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxylate (9.25 g, 37.4 mmol) and N-(2,4-dimethoxybenzyl)-aniline (9.10 g, 37.4 mmol) in heptane (200 mL) was stirred at 110° C. under a flow of N2 for 6 h letting the EtOH evaporate from the reaction mixture. The product started to precipitate and some extra heptane was added. The reaction mixture was then stirred at 100° C. overnight, still under a gentle flow of N2. The product (12.21 g, 73%) crystallized from the reaction mixture and was collected by filtration while still warm (ca 50° C.).

Workup

customevaporate from the reaction mixture
customto precipitate
additionsome extra heptane was added
customThe product (12.21 g, 73%) crystallized from the reaction mixture
filtrationwas collected by filtration
temperaturewhile still warm (ca 50° C.)

Sources & evidence

ORD record: ord-f1f8ab7392a64bb29b98e0cee720559c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962598B2

Reaction notes

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