Diethyl (ethoxymethylene)malonate → Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 347881Notes

Reaction equation

[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][CH:10]=1)[NH:11][CH:27]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:20]2=[O:19]

Participants

Conditions

Temperature: 250 °C

Procedure

4-(2,3-Dichlorobenzyl)phenylamine (10.0 g, 39.7 mmol) obtained in Step 2 was dissolved in toluene (100 ml) and diethyl ethoxymethylenemalonate (8.8 ml, 43.7 mmol) was added. The mixture was heated under reflux for 3 hrs. The reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml) was added to dissolve the residue. The mixture was stirred with heating at 250° C. for 3 hrs. After allowing the mixture to cool, n-hexane was added to the reaction solution and the precipitate was collected by filtration, washed with chloroform and vacuum-dried to give an object product (10.1 g, yield 68%) as a pale-yellow solid.

Workup

temperatureThe mixture was heated
temperatureunder reflux for 3 hrs
concentrationThe reaction solution was concentrated under reduced pressure, and diphenyl ether (100 ml)
additionwas added
dissolutionto dissolve the residue
temperatureto cool
additionn-hexane was added to the reaction solution
filtrationthe precipitate was collected by filtration
washwashed with chloroform
customvacuum-dried

Sources & evidence

ORD record: ord-16a13797cb3b44ebb45853603a229f76
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176220B2

Reaction notes

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