Phosphorus oxychloride → Isoquinoline, 1-chloro-

温度

17.5 °C

69.3 g of isoquinoline N-oxide (448 mmol) manufactured by Tokyo Chemical Industry Co., Ltd. and 225 ml of chloroform were introduced into a 1 L-three-neck flask dissolved therein. Then, 219.6 g (1,432 mmol) of phosphorous oxychloride was slowly added dropwise therein and stirred under ice-cooling while maintaining the inner temperature at 15 to 20° C. Thereafter, the mixture was heated and stirred under reflux for 3 hours. The reaction product was left to cool to room temperature, and the resulting product was poured into ice water. The mixture was extracted with ethyl acetate, and the organic layer was washed with water until it was neutral. The solvent was then dried under reduced pressure. The residue was purified using silica gel column chromatography (eluent: chloroform/hexane: 5/1) to yield 35.5 g of 1-chloroisoquinoline white crystals (44.9% yield).

1. dissolutiondissolved
2. temperaturecooling
3. temperatureThereafter, the mixture was heated
4. stirringstirred
5. temperatureunder reflux for 3 hours
6. waitThe reaction product was left
7. temperatureto cool to room temperature
8. extractionThe mixture was extracted with ethyl acetate
9. washthe organic layer was washed with water until it
10. customThe solvent was then dried under reduced pressure
11. customThe residue was purified

ORDレコード

ord-a7fe4827bf244e3ca18040ef561605d5

出典データセット

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07604683B2