Ammonia → 6-Chloro-5-(trifluoromethyl)pyridin-2-amine

Temperatur

93 °C

2,6-Dichloro-3-(trifluoromethyl)pyridine (5.00 g, 23.2 mmol) and 28% aqueous ammonia (150 mL) were placed in a 250 mL autoclave. The mixture was heated at 93° C. for 21 h. The reaction was cooled to rt and extracted with EtOAc (100 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (2-20% EtOAc in petroleum ether as eluant) to give 6-chloro-5-(trifluoromethyl)pyridin-2-amine (2.1 g, 46% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.69 (d, J=8.4 Hz, 1H), 7.13 (br s, 2H), 6.43 (d, J=8.4 Hz, 1H). MS (ESI) m/z (M+H)+197.2

1. temperatureThe reaction was cooled to rt
2. extractionextracted with EtOAc (100 mL×3)
3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
4. customevaporated under vacuum
5. customto give the crude product, which
6. customwas purified by column chromatography on silica gel (2-20% EtOAc in petroleum ether as eluant)

ORD-Eintrag

ord-278ad5d8ec7446beadfd5a43a5f4f93a

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08741933B2