Thionyl Chloride → HCID 13295785, compound

A solution of 3-(8-quinolinyloxy)-1-propanol (32.0 g, 0.158 mole) and thionyl chloride (24.0 g, 0.203 mole) was heated at reflux for 5 hours in 300 ml of dry benzene (dried over 4 A molecular sieves). The reaction mixture was cooled to room temperature and then stripped to dryness. The residue was treated with potassium carbonate solution (30 g in 500 ml of water). The gummy residue was dissolved in chloroform and extracted with the potassium carbonate solution. The chloroform layer was dried over anhydrous sodium sulfate, filtered, and solvent removed to give a dark mass which crystallized. The mass was treated with 500 ml of boiling hexane. The hexane layer was decanted off from insoluble oil. A white solid crystallized on cooling, the hexane layer was filtered off. The solid was dried in vacuo at room temperature overnight to give 26.69 g (76.2%) of white cyrstalline solid, m.p. 69°-71° C.

1. customdried over 4 A molecular sieves)
2. additionThe residue was treated with potassium carbonate solution (30 g in 500 ml of water)
3. dissolutionThe gummy residue was dissolved in chloroform
4. extractionextracted with the potassium carbonate solution
5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. customsolvent removed
8. customto give a dark mass which
9. customcrystallized
10. additionThe mass was treated with 500 ml of boiling hexane
11. customThe hexane layer was decanted off from insoluble oil
12. customA white solid crystallized
13. temperatureon cooling
14. filtrationthe hexane layer was filtered off
15. customThe solid was dried in vacuo at room temperature overnight
16. customto give 26.69 g (76.2%) of white cyrstalline solid, m.p. 69°-71° C.

ORD record

ord-41fa86e6475645fa8b1e1f11c948bfec

Source dataset

uspto-grants-1989_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04810713