8-氨基喹啉 → 4-氯-8-氨基喹啉

HRID 1663306笔记

反应方程式

HRID 1663306 反应方程式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Cl:12]N1C(=O)CCC1=O>CC(O)C>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[Cl:12]

参与物

4

反应物 2

HCID 113598-氨基喹啉HCID 31398N-氯代丁二酰亚胺

产物 1

HCID 126042744-氯-8-氨基喹啉收率 34%

试剂、催化剂与溶剂 1

HCID 3776异丙醇溶剂

反应条件

温度
25 °C

实验过程

8-amino quinoline (4.5 g, 31.3 mmol), N-chlorosuccinimide (4.80 g, 36 mmol) was taken up in iPrOH (50 mL) at 60° C. The mixture was heated to reflux and stirred for 20 min. The solution was cooled to 25° C. and concentrated to ⅓ original volume. The mixture was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography (5:1 hexanes/EtOAc) to afford 1.90 g (34%) of a 8-amino-4-chloro-quinoline product.

后处理

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customThe mixture was partitioned between CH2Cl2 and water
  5. extractionThe aqueous layer was extracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (5:1 hexanes/EtOAc)

来源与证据

ORD记录
ord-b7a6a4e82fbe4705bdfc9e68ad8bd688
来源数据集
uspto-grants-2011_10
专利号
US08034933B2

反应笔记

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