Toluene → (3-Fluorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanone

HRID 1633366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633366
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1)=[O:5].Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[F:12][C:8]1[CH:7]=[C:6]([C:4]([C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=2[NH:1][C:18]2[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=2)=[O:5])[CH:11]=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 796132-Chloro-3-nitropyridineHCID 22312228(2-Aminophenyl)(3-fluorophenyl)methanone

Produkt 1

HCID 13388388(3-Fluorophenyl){2-[(3-nitropyridin-2-yl)amino]phenyl}methanoneAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Under nitrogen atmosphere, 45.0 g (0.209 mole) of 2-amino-3'-fluorobenzophenone was added in four portions at 15 min intervals to a stirred melt (120°-125° C.) of 38.2 g (0.241 mole) of 2-chloro-3-nitropyridine. The reaction mixture was heated at 120°-125° C. for one hr. and then at 145°-150° C. for 45 min. The mixture was cooled to 130° C. and 100 ml of toluene was added. The cooled mixture (room temperature) was diluted with 100 ml of ethyl acetate and extracted with 100 ml of 10% potassium hydroxide. The organic layer was extracted with three 100 ml portions of 3N hydrochloric acid, 100 ml of water and 50 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from ethyl acetate-isopropyl ether to give 35.5 g (50%) solid. The solid was dissolved in 200 ml of methylene chloride and the solution stirred with 50 g of fluorisil for 2 hr. The mixture was filtered and the filtrate was concentrated in vacuo. A 5 g portion of the residue was recrystallized from ethyl acetate-isopropyl ether to give 4.1 g of yellow-orange solid, m.p. 98°-101° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 120°-125° C. for one hr
  2. extractionextracted with 100 ml of 10% potassium hydroxide
  3. extractionThe organic layer was extracted with three 100 ml portions of 3N hydrochloric acid, 100 ml of water and 50 ml of saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from ethyl acetate-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-899c4d269e654c3e8e7471c3ed6e61c9
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04480100

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