Hydrochloric Acid → 4-Chloropyridin-2-amine--hydrogen chloride (1/1)

Temperature

100 °C

To a solution of 4-chloro-2-pyridinecarboxylic acid (5.95 g) in tert-butanol (89.25 mL) were added triethylamine (6.32 mL) and diphenylphosphoryl azide (8.95 mL). The mixture was stirred at 100° C. for overnight. To the solution was added water and the mixture was extracted with EtOAc and washed with water and brine. The extract was dried over MgSO4 and concentrated under reduced pressure. The residue was recrystallized with EtOAc to give a white solid. The solid was dissolved in dioxane (50 mL). To the solution was added 4M HCl in dioxane (90 mL) and the mixture was stirred at ambient temperature overnight. The mixture was concentrated under reduced pressure to give 4-chloro-2-pyridinamine hydrochloride (3.02 g) as a white solid.

1. extractionthe mixture was extracted with EtOAc
2. washwashed with water and brine
3. dry with materialThe extract was dried over MgSO4
4. concentrationconcentrated under reduced pressure
5. customThe residue was recrystallized with EtOAc
6. customto give a white solid
7. stirringthe mixture was stirred at ambient temperature overnight
8. concentrationThe mixture was concentrated under reduced pressure

ORD record

ord-b30eb359faba4260b8476a08651b3750

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163767B2