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), and the solution was added with cyclopropanecarbonylchloride (4.0 mL, 43.5), followed by stirring at 50° C. for 3 hr. Methanol (10 mL) and aqueous ammonia (9 mL) were added to the reaction mixture, 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) and the solution was added with ferrous sulfate 7 hydrate (13.86 g, 49.9 mmol) and aqueous ammonia (19 mL), followed by stirring at 50° C. for 4 hr. The reaction mixture was filtrated, 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 reaction mixture was concentrated under reduced pressure, and the residue was neutralized with aqueous sodium hydroxide solution, and the mixture was 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. stirringby stirring at 50° C. for 4 hr
4. filtrationThe reaction mixture was filtrated
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 reaction mixture was concentrated under reduced pressure
12. extractionthe mixture was extracted 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-3d76f6656bf24902a31e60f09e509334

Quelldatensatz

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08242151B2