Aniline → 3-nitro-N-phenylpyridin-4-amine

HRID 1491637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1491637
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCOCC1>[C:12]1([NH:11][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 8471TriethylamineHCID 27357814-Chloro-3-nitropyridine

Produkt 1

HCID 6120053-nitro-N-phenylpyridin-4-amineAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4-Chloro-3-nitropyridine (1.50 g, 9.46 mmol) and aniline (2.0 ml, 21.9 mmol) were dissolved in 10 ml of 1,4-dioxane, and 2 ml of triethylamine was added thereto, followed by reaction at 80° to 90° C. for 2 hours. Then, the solvent was removed by distillation under reduced pressure, and 10 ml of hexane was added to the residue to wash it. The solvent was removed by decantation. The residue was further similarly treated with 10 ml of ether. The residue was purified by silica gel column chromatography [eluent: hexane:ethyl acetate=2:1 (v/v)] to obtain 1.41 g of a yellow solid (yield: 68.8%).

Aufarbeitung

  1. customfollowed by reaction at 80° to 90° C. for 2 hours
  2. customThen, the solvent was removed by distillation under reduced pressure, and 10 ml of hexane
  3. additionwas added to the residue
  4. washto wash it
  5. customThe solvent was removed by decantation
  6. additionThe residue was further similarly treated with 10 ml of ether
  7. customThe residue was purified by silica gel column chromatography [eluent: hexane:ethyl acetate=2:1 (v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-2907bb8d890f46139420943e4de0f343
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371086

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