Pyridine → methyl 2-fluoro-3-(N-methylbenzamido)benzoate

HRID 1053616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053616
[F:1][C:2]1[C:10]([NH:11][CH3:12])=[CH:9][CH:8]=[CH:7]C=1C(O)=O.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.[C:28]([O:31][CH2:32]C)(=[O:30])[CH3:29]>O1CCCC1>[F:1][C:2]1[C:10]([N:11]([CH3:12])[C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=[CH:7][C:29]=1[C:28]([O:31][CH3:32])=[O:30]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 200866302-Fluoro3-(methylamino)benzoic acid

Produkt 1

HCID 58298654methyl 2-fluoro-3-(N-methylbenzamido)benzoateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Fluoro3-(methylamino)benzoic acid (1.42 g, 4.94 mmol) was dissolved in tetrahydrofuran (15 ml), and benzoyl chloride (0.83 g, 5.90 mmol) and pyridine (0.47 g, 5.94 mmol) were added thereto. The reaction mixture was allowed to react for 12 hours at room temperature. Ethyl acetate was added to the reaction solution, and the mixture was washed sequentially with water, a 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate. The sodium sulfate was filtered away, and the concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/8), as a result of which 1.42 g (yield: 64%) of the indicated compound was obtained.

Aufarbeitung

  1. customto react for 12 hours at room temperature
  2. washthe mixture was washed sequentially with water
  3. dry with materiala 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate, and saturated saline, and then dried over anhydrous sodium sulfate
  4. filtrationThe sodium sulfate was filtered away
  5. customthe concentration residue was purified by silica gel column chromatography (developer solvent: ethyl acetate/n-hexane=1/8)

Quellen und Nachweise

ORD-Eintrag
ord-c7052637915a48a28e95e847bdb51552
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394240B2

Notizen zur Reaktion

Wird geladen…