HCID 22485103, compound → HCID 22484980, compound

To a solution of 6-bromo-2-[N-(2-chloro-4-phenylbenzyl)-amino]-3-nitropyridine (13.5 g) in acetic acid (27 ml) and ethanol (81 ml) was added iron powder (7.2 g) at room temperature under a nitrogen flow, and the mixture was refluxed under heating. After 2 hr, the reaction mixture was cooled, filtered through celite, and washed with ethyl acetate. The filtrate was concentrated and subjected to azeotropic distillation twice with toluene. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the residue and the mixture was stirred at room temperature for 10 min. This mixture was filtered through celite and washed with ethyl acetate. The organic layer was separated, washed with saturated brine and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated and the residue was applied to flash silica gel column chromatography (silica gel, 400 ml) and eluted with hexane:ethyl acetate=5:1-3:1-2:1 to give 3-amino-6-bromo-2-[N-(2-chloro-4-phenylbenzyl)amino]pyridine (10.6 g) as a black gum.

1. temperaturethe mixture was refluxed
2. temperatureunder heating
3. temperaturethe reaction mixture was cooled
4. filtrationfiltered through celite
5. washwashed with ethyl acetate
6. concentrationThe filtrate was concentrated
7. distillationsubjected to azeotropic distillation twice with toluene
8. additionEthyl acetate and saturated aqueous sodium hydrogen carbonate solution were added to the residue
9. filtrationThis mixture was filtered through celite
10. washwashed with ethyl acetate
11. customThe organic layer was separated
12. washwashed with saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationAfter filtration
15. concentrationthe filtrate was concentrated
16. washeluted with hexane

ORD record

ord-40477df2f4df41e99ed141e60c9dc8e8

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06573274B1