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

HRID 257418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257418
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.CCCCCC>O1CCOCC1.C(OCC)(=O)C>[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

7

Edukt 4

HCID 6115AnilineHCID 8058HexaneHCID 8471TriethylamineHCID 27357814-Chloro-3-nitropyridine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 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

Quellen und Nachweise

ORD-Eintrag
ord-cc2b8301bd004cb5afc5f1553d52a2bf
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262415

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