Diethyl (ethoxymethylene)malonate → Ethyl 6-(2,3-dichlorobenzyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate
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
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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), diethyl ethoxymethylenemalonate (8.8 ml, 43.7 mmol) was added, and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, diphenyl ether (100 ml) was added to the residue to allow dissolution, and the mixture was stirred with heating at 250° C. for 3 hr. After allowing to cool, n-hexane was added to the reaction mixture, The precipitated solid was collected by filtration, washed with chloroform, and vacuum dried to give the object product (10.1 g, yield 68%) as a pale-yellow solid.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 3 hr
- concentrationThe reaction mixture was concentrated under reduced pressure, diphenyl ether (100 ml)
- additionwas added to the residue
- dissolutiondissolution
- temperatureto cool
- additionn-hexane was added to the reaction mixture
- filtrationThe precipitated solid was collected by filtration
- washwashed with chloroform, and vacuum
- customdried
Sources & evidence
- ORD record
- ord-22813655ac2d4c52bb9383a9e19873a5
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531554B2
Reaction notes
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