Benzyl Chloride → 2-Amino-3-benzyloxypyridine

Temperature

25 °C

In a 12 liter 3-neck round bottom flask equipped with a mechanical stirrer and thermometer there were placed 2.5 liters of 40% sodium hydroxide solution, 26.5 g of Adogen 464 (Reg. Trademark) and 2.5 liters of dichloromethane. To this vigorously stirred mixture was added 550 g of 2-amino-3-hydroxypyridine. The temperature was 38° C. The brown orange mixture was cooled to 25° C., and 677.5 g of benzylchloride was added in one portion, stirred 16 hr. and the mixture was allowed to separate into 2 phases. The lower aqueous phase was separated and diluted with 1 liter of ice:water. This solution was then extracted with dichloromethane (3×15 liters). The combined dichloromethane extractswere added to the original dichloromethane phase, washed with 1 liter of saturated sodium chloride solution and dried over potassium carbonate. Thedichloromethane extract was filtered and concentrated on the rotary evaporator to an orange solid. This solid was dissolved in 1 liter of boiling absolute ethanol, and the solution was filtered. The filtrate was chilled, and the crystals that formed were filtered, washed with 500 ml ofethanol at -10° C., and dried at 50° C. in a vacuum oven, to give the desired product.

1. customIn a 12 liter 3-neck round bottom flask equipped with a mechanical stirrer
2. customwas 38° C
3. customto separate into 2 phases
4. customThe lower aqueous phase was separated
5. additiondiluted with 1 liter of ice
6. extractionThis solution was then extracted with dichloromethane (3×15 liters)
7. additionThe combined dichloromethane extractswere added to the original dichloromethane phase
8. washwashed with 1 liter of saturated sodium chloride solution
9. dry with materialdried over potassium carbonate
10. filtrationThedichloromethane extract was filtered
11. concentrationconcentrated on the rotary evaporator to an orange solid
12. dissolutionThis solid was dissolved in 1 liter
13. filtrationthe solution was filtered
14. temperatureThe filtrate was chilled
15. customthe crystals that formed
16. filtrationwere filtered
17. washwashed with 500 ml ofethanol at -10° C.
18. customdried at 50° C. in a vacuum oven

ORD record

ord-32a9f575728d42fc88420cb865191c8d

Source dataset

uspto-grants-1984_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04450164