4-Chloroquinoline → HCID 19094094, compound
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]2[C:26](=[O:27])[NH:25][C:24](=[O:28])[NH:23][C:22]2=[O:29])=[CH:15][CH:14]=1>>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]2([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=[CH:4][CH:3]=3)[C:22](=[O:29])[NH:23][C:24](=[O:28])[NH:25][C:26]2=[O:27])=[CH:15][CH:14]=1Participants
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 3.63 g of 4-chloroquinoline and 5.3 g of 5-[2-(4-chlorophenyl)ethyl]barbituric acid was heated to 150° C. for 11/4 hours, to form 5-[2-(4-chlorophenyl)ethyl]-5-(4-quinolinyl)barbituric acid. This compound was hydrolyzed, without isolation, by adding 4 g of NaOH in 40 ml of water and refluxing for four hours. The mixture was cooled, acidified with HCl and refluxed for several hours, cooled, and neutralized with dilute NaOH. The desired product was extracted into CH2Cl2, which was then filtered through phase separating paper and evaporated to dryness. The residue was absorbed onto silica gel and chromatographed over silica gel using CH2Cl2. Fractions containing product were combined to give 2.69 g of crystalline material. This was recrystallized from a petroleum ether/CH2Cl2 mixture to give 2.35 g of the title product. Yield: 39%. M.P. 97° C.
Sources & evidence
- ORD record
- ord-d840f80355ff4a85bbe1943b04c61971
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05114939
Reaction notes
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