Hydrochloric Acid → HCID 77230825, compound

Temperature

-5 °C

6-Chloro-3-nitro-N-(prop-2-en-1-yl)pyridin-2-amine (71-2, 11.07 g, 51.8 mmol, 1.0 equiv) was added to concentrated HCl (106 mL) to give a suspension. The resulting reaction contents were cooled to −5° C. Tin(II) chloride dehydrate (70.2 g, 311 mmol, 6.0 equiv) was then added in seven 10-g portions while maintaining an internal temperature below 0° C. Following the addition, the reaction mixture was then transferred to a 90° C. bath. After 1 h at 90° C., the reaction contents were cooled to RT and added dropwise to 10N NaOH (300 mL) at 0° C. with vigorous stirring. Following the addition, the mixture was warmed to RT and stirred for 10 min. The aqueous layer was then extracted with 3×100 mL EtOAc and the combined organics were dried over Na2SO4, filtered and concentrated to give a thick, purple oil. The crude material was carried onward without further purification. LRMS (M+H)+: observed=189.0, calculated=183.6.

1. customto give a suspension
2. customThe resulting reaction contents
3. temperaturewhile maintaining an internal temperature below 0° C
4. additionthe addition
5. customwas then transferred to a 90° C.
6. customthe reaction contents
7. temperaturewere cooled to RT
8. additionthe addition
9. temperaturethe mixture was warmed to RT
10. extractionThe aqueous layer was then extracted with 3×100 mL EtOAc
11. dry with materialthe combined organics were dried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated
14. customto give a thick, purple oil
15. customThe crude material was carried onward without further purification

ORD record

ord-0442c838d7c74d89afbc53a7b7b8d621

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765784B2