Ammonia → HCID 178477974, Verbindung

Temperatur

50 °C

2-Chloro-6-nitroaniline (3.00 g, 17.4 mmol) and pyridine (7.0 mL, 86.9 mmol) were dissolved in DMA (17 mL), cyclopropanecarbonyl chloride (4.0 mL, 43.5) was added and the mixture was stirred at 50° C. for 3 hr. To the mixture were added methanol (10 mL) and aqueous ammonia (9 mL), and the mixture was stirred at room temperature for 30 min. Water (10 mL) was added, and the precipitated solid was collected by filtration. The solid was suspended in ethanol (38 mL) and water (38 mL), ferrous sulfate 7 hydrate (13.86 g, 49.9 mmol) and aqueous ammonia (19 mL) were added, and the mixture was stirred at 50° C. for 4 hr. The mixture was filtered, and the filtrate was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Acetic acid (8 mL) was added to the residue, and the mixture was stirred at 90° C. for 1 hr. The mixture was concentrated under reduced pressure, neutralized with aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Ethyl acetate (5 mL) and diisopropyl ether (5 mL) were added to the residue, and the precipitated solid was collected by filtration to give the title compound (1.20 g, 36%).

1. stirringthe mixture was stirred at room temperature for 30 min
2. filtrationthe precipitated solid was collected by filtration
3. stirringthe mixture was stirred at 50° C. for 4 hr
4. filtrationThe mixture was filtered
5. extractionthe filtrate was extracted with ethyl acetate
6. washwashed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. additionAcetic acid (8 mL) was added to the residue
10. stirringthe mixture was stirred at 90° C. for 1 hr
11. concentrationThe mixture was concentrated under reduced pressure
12. extractionextracted with ethyl acetate
13. washThe organic layer was washed with brine
14. dry with materialdried over anhydrous magnesium sulfate
15. concentrationconcentrated under reduced pressure
16. additionEthyl acetate (5 mL) and diisopropyl ether (5 mL) were added to the residue
17. filtrationthe precipitated solid was collected by filtration

ORD-Eintrag

ord-13c6cecab68143abbcd75a9c669c9bae

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08486980B2