Diethyl (ethoxymethylene)malonate → HCID 1486467, compound
Reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>>[C:4]([C:3]1[CH:12]=[C:13]([Cl:16])[CH:14]=[C:15]2[C:2]=1[NH:1][CH:27]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:20]2=[O:19])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1Participants
Procedure
2-Amino-5-chlorobenzophenone (3.0 g) and diethyl ethoxymethylenemalonate (3.3 g) were reacted in the same manner as in Experimental Example 1 to give 8-benzoyl-6-chloro-3-ethoxycarbonyl-4(1H)-quinolone (2.1 g). The compound (1.4 g) was dissolved in methanol (24 ml). A 10% aqueous solution of NaOH (16 ml) was added to the solution, and the mixture was heated under reflux for 1 hour. After acidification of the mixture with a 10% aqueous solution of HCl, the precipitate was collected by filtration, washed with water and dried to give a carboxylic acid (1.2 g). The carboxylic acid (1.2 g) was suspended in diphenyl ether (30 ml), and the suspension was heated under reflux under a stream of argon at 280° C. for 3 hours. After the reaction mixture was left to cool, a mixed solvent of ether (50 parts) and n-hexane (50 parts) was added, and the crude crystal thus obtained was collected by filtration and recrystallized from chloroform-methanol-n-hexane to give 8-benzoyl-6-chloro-4(1H)-quinolone (compound 18, 0.6 g).
Sources & evidence
- ORD record
- ord-e29470f8ed734d159cafc129667acbfe
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05081121
Reaction notes
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