Ethanol → HCID 86628514, compound

Temperature

85 °C

Iron (67.3 g) and ammonium chloride (129 g) were added to a solution of 5-bromo-3-methoxy-2-nitropyridine (56.0 g, CAS #152684-26-9) in ethanol (500 mL) and water (200 mL). The reaction solution was stirred at 80 to 90° C. for one hour and then left to cool to room temperature. The reaction solution was filtered through celite and washed with ethanol. Then, the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate and water, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was diluted with THF (84 mL). The THF solution was added dropwise to a mixed solution of formic acid (78.1 mL) and acetic anhydride (78.3 mL) at room temperature. Then, the reaction solution was stirred for one hour. Ice water (500 mL) was added to the reaction solution, and the precipitated crystals were collected by filtration. The crystals were washed with water and then air-dried. The crystals were recrystallized from toluene to obtain 34.1 g of the title compound. The property values of the compound are as follows.

1. waitleft
2. temperatureto cool to room temperature
3. filtrationThe reaction solution was filtered through celite
4. washwashed with ethanol
5. concentrationThen, the filtrate was concentrated under reduced pressure
6. additionThe residue was diluted with ethyl acetate and water
7. customthe organic layer was separated
8. washThe resulting organic layer was washed with brine
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. additionThe residue was diluted with THF (84 mL)
12. additionThe THF solution was added dropwise to a mixed solution of formic acid (78.1 mL) and acetic anhydride (78.3 mL) at room temperature
13. stirringThen, the reaction solution was stirred for one hour
14. additionIce water (500 mL) was added to the reaction solution
15. filtrationthe precipitated crystals were collected by filtration
16. washThe crystals were washed with water
17. customair-dried
18. customThe crystals were recrystallized from toluene

ORD record

ord-43bc8a557ab743afbf13ad67e5120c0f

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754100B2