4-Chloroquinoline → HCID 19094094、化合物
反応式
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]=1参加物
反応条件
- 温度
- 150 °C
実験手順
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.
出典と根拠
- ORDレコード
- ord-d840f80355ff4a85bbe1943b04c61971
- 出典データセット
- uspto-grants-1992_05
- 特許番号
- US05114939
反応ノート
読み込み中…