Hydrochloric Acid → 4-Chloro-3-(pyridin-2-yl)aniline

Temperature

60 °C

4-chloro-3-(pyridin-2-yl)nitrobenzene (1.47 g, 6.26 mmol) was suspended in EtOH (35 mL), and the SnCl2 (3.87 g; 20.4 mmol) and conc. HCl (5 mL) were added and rinsed in with a further 5 mLs EtOH. The solution was placed in a 40° C. oil bath and heated to 60° C. The solution was stirred at 60° C. for 1½ hr., cooled to RT and diluted with 1 N HCl (100 mL). This solution was poured into an Et2O/1 N HCl solution (100 mL:150 mL) and extracted. The aqueous layer was diluted with EtOAc (250 mL), cooled to 0° C., and made basic with 10 N NaOH (50 mL). This solution was extracted (EtOAc, 2×), and the combined organics were washed with brine and dried over Na2SO4 and charcoal. Suction filtration through celite gave a clear colorless solution which was concentrated to yield 4-chloro-3-(pyridine-2-yl)aniline (1.21 g, 5.93 mmol, 94% yield) as a cream colored crystalline solid which was used in the next reaction without further purification.

1. washrinsed in with a further 5 mLs EtOH
2. customwas placed in a 40° C.
3. temperature, cooled to RT
4. additiondiluted with 1 N HCl (100 mL)
5. additionThis solution was poured into an Et2O/1 N HCl solution (100 mL:150 mL)
6. extractionextracted
7. additionThe aqueous layer was diluted with EtOAc (250 mL)
8. temperaturecooled to 0° C.
9. extractionThis solution was extracted (EtOAc, 2×)
10. washthe combined organics were washed with brine
11. dry with materialdried over Na2SO4 and charcoal
12. filtrationSuction filtration through celite
13. customgave a clear colorless solution which
14. concentrationwas concentrated

ORD record

ord-7af9a87e35454c0f974150174e6f179e

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321761B2