三氯甲烷 → 1-氯异喹啉

HRID 1408279

反应方程式

HRID 1408279 反应方程式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N+:2]=1[O-].C(Cl)(Cl)[Cl:13].P(Cl)(Cl)(Cl)=O>O>[Cl:13][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

参与物

5

反应物 3

HCID 6212三氯甲烷HCID 24813三氯氧磷HCID 290378异喹啉-N-氧化物

产物 1

HCID 1405391-氯异喹啉收率 44.9%

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

69.3 g (448 mmol) of isoquinoline N-oxide (made by Tokyo Kasei) and 225 ml of chloroform were placed and dissolved in a 1 liter-three-necked flask, and under stirring and cooling with ice, 219.6 g (1432 mmol) of phosphorus oxychloride was gradually added dropwise thereto while the internal temperature was held at 15-20° C. Thereafter, the temperature was raised, and reflux under stirring was performed for 3 hours. The reaction product was cooled by standing to room temperature and poured into iced water. After extraction with ethyl acetate, the organic layer washed with water until neutrality, and the solvent was removed under a reduced pressure to provide a dry solid, which was then purified by silica gel column chromatography (eluent: chloroform/hexane=5/1) to obtain 35.5 g (yield: 44.9%) of 1-chloroisoquinoline white crystal.

后处理

  1. dissolutiondissolved in a 1 liter-three-necked flask
  2. additionwas gradually added dropwise
  3. customwas held at 15-20° C
  4. temperatureThereafter, the temperature was raised
  5. temperaturereflux
  6. stirringunder stirring
  7. temperatureThe reaction product was cooled
  8. customby standing to room temperature
  9. extractionAfter extraction with ethyl acetate
  10. washthe organic layer washed with water until neutrality
  11. customthe solvent was removed under a reduced pressure
  12. customto provide a dry solid, which
  13. customwas then purified by silica gel column chromatography (eluent: chloroform/hexane=5/1)

来源与证据

ORD记录
ord-8cce558fce8547ad88046052dfd12cee
来源数据集
uspto-grants-2014_12
专利号
US08920943B2

关联笔记

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