Chloroform → Isoquinoline, 1-chloro-

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.

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)

ORD-Eintrag

ord-8cce558fce8547ad88046052dfd12cee

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08920943B2