Hydrogen Bromide → 2-Bromo-4-nonadecylpyridine

Temperatur

-20 °C

Powdered 2-amino-4-nonadecylpyridine (110.6 g, 0.31 mol) was added under vigorous stirring in portions to 48% hydrobromic acid (500 mL) at 20 to 30° C. in a 4-L glass reactor. After all of the compound was dissolved, the mixture was cooled at −20° C. To this suspension was added cooled bromine (44.3 mL, 0.86 mol) dropwise over 30 min, maintaining the temperature at −20° C. The resulting paste was stirred for 90 min at this temperature. Then sodium nitrite (56.6 g, 0.82 mol) in water (250 mL) was added dropwise. After that the reaction mixture was allowed to warm to 15° C. over 1 h and was stirred for an additional 45 min. The mixture was cooled to −20° C. and treated with cooled aqueous NaOH (222 g, 330 mL H2O). During the addition the temperature was kept at −10° C. maximum. The mixture was allowed to warm to room temperature and stirred for 1 h. The mixture was extracted with ethyl acetate, the organic phase was dried with Na2SO4, and the solvent was removed in vacuo. The residue was subjected to distillation in vacuo to yield the desired. Yield 50%. Anal. Calcd for C24H42BrN: C, 67.90; H, 9.97; N, 3.30. Found: C, 67.50; H, 9.87; N, 3.40. MS (ESIMS): m/z: 423.3.

1. dissolutionAfter all of the compound was dissolved
2. additionTo this suspension was added
3. temperaturemaintaining the temperature at −20° C
4. temperatureto warm to 15° C. over 1 h
5. stirringwas stirred for an additional 45 min
6. temperatureThe mixture was cooled to −20° C.
7. additionDuring the addition the temperature
8. customwas kept at −10° C.
9. temperatureto warm to room temperature
10. stirringstirred for 1 h
11. extractionThe mixture was extracted with ethyl acetate
12. dry with materialthe organic phase was dried with Na2SO4
13. customthe solvent was removed in vacuo
14. distillationThe residue was subjected to distillation in vacuo
15. customto yield the

ORD-Eintrag

ord-1bb8c35ebde4470584adc13484d93ee8

Quelldatensatz

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07812251B2