Pyridine → HCID 68526474, Verbindung

To a mixture of 2-amino-4-nitro-benzonitrile (3.3 g, 20.23 mmol) and pyridine (4.88 ml, 60.68 mmol) in anhydrous tetrahydrofuran (30 ml) under an atmosphere of nitrogen was added 4-fluorobenzoyl chloride (2.67 ml, 22.25 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. Then more 4-fluorobenzoyl chloride (2.67 ml, 22.25 mmol) was added to the mixture. The reaction mixture was stirred at 50° C. for 1 hour. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydrogen carbonate (saturated). The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was dissolved in methanol (200 ml) and potassium carbonate (5.1 g) was added. The reaction mixture was stirred for 16 hours at ambient temperature. The reaction mixture was diluted with ethyl acetate and aqueous sodium hydrogen carbonate (saturated). The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/tetrahydrofuran 10:1) to give N-(2-cyano-5-nitro-phenyl)-4-fluoro-benzamide (1.82 g, 32% yield). 1H-NMR (DMSO-d6, 400 MHz): 11.02 (s, 1H), 8.48 (s, 1H), 8.20 (s, 2H), 8.11 (m, 2H), 7.45 (m, 2H) ppm.

1. stirringThe reaction mixture was stirred at 50° C. for 1 hour
2. customThe phases were separated
3. extractionthe aqueous phase was extracted twice with ethyl acetate
4. dry with materialThe combined organic phases were dried over sodium sulfate
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in methanol (200 ml)
7. additionpotassium carbonate (5.1 g) was added
8. stirringThe reaction mixture was stirred for 16 hours at ambient temperature
9. additionThe reaction mixture was diluted with ethyl acetate and aqueous sodium hydrogen carbonate (saturated)
10. customThe phases were separated
11. extractionthe aqueous phase was extracted twice with ethyl acetate
12. dry with materialThe combined organic phases were dried over sodium sulfate
13. concentrationconcentrated
14. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/tetrahydrofuran 10:1)

ORD-Eintrag

ord-b9e1ab43f93042b6a3f9bba9521fff61

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08466180B2