Hydrochloric Acid → HCID 135749777, compound

Hydrogen chloride gas was bubbled through a chilled solution of p-cyanophenol (30 g, 0.25 mole) in methanol (120 mo) for 70 min. The heavy suspension was stoppered and stirred overnight. After cooling in an ice bath, the solid was collected by filtration and rinsed twice with cold methanol. The solid was dried under nitrogen to give 46.56 g. The solid iminoether was resuspended in methanol (150 ml) and treated with methylamino acetaldehyde dimethyl acetal (42 ml, 0.325 m) and then heated at reflux temperature for 3 hr. The reaction was then concentrated to an oil which was redissolved in 2N hydrochloric acid solution (200 ml). The solution was then concentrated to remove the methanol and the resulting aqueous solution was extracted twice with methylene chloride and then made basic first with 50% sodium hydroxide solution and finishing up with 10% sodium bicarbonate solution. The solid was collected and rinsed with water, 2-propanol and isopropyl ether. The solid was dissolved in methanol, treated with charcoal and filtered. The filtrate was partially concentrated by boiling and replacing the methanol with 2-propanol, from which a white, crystalline solid precipitated out of solution. The solid was filtered and dried (14.4 g, 0.083 mole, 66.7% yield, mp 239°-242° C.).

1. temperatureAfter cooling in an ice bath
2. filtrationthe solid was collected by filtration
3. washrinsed twice with cold methanol
4. customThe solid was dried under nitrogen
5. customto give 46.56 g
6. temperatureheated
7. temperatureat reflux temperature for 3 hr
8. concentrationThe reaction was then concentrated to an oil which
9. dissolutionwas redissolved in 2N hydrochloric acid solution (200 ml)
10. concentrationThe solution was then concentrated
11. customto remove the methanol
12. extractionthe resulting aqueous solution was extracted twice with methylene chloride
13. customThe solid was collected
14. washrinsed with water, 2-propanol and isopropyl ether
15. dissolutionThe solid was dissolved in methanol
16. additiontreated with charcoal
17. filtrationfiltered
18. concentrationThe filtrate was partially concentrated
19. customfrom which a white, crystalline solid precipitated out of solution
20. filtrationThe solid was filtered
21. customdried (14.4 g, 0.083 mole, 66.7% yield, mp 239°-242° C.)

ORD record

ord-8222850daf54409691c8bddadd46ee93

Source dataset

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05025031