Ammonia → 5-Phenyl-2-pyridinamine

HRID 1112519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1112519
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1.[Na].N.[Cl-].[NH4+].[NH2:18]C1C=CC(CCCC)=CN=1>C(OCC)C>[NH2:18][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1

Komponenten

7

Edukt 5

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 27628682-Chloro-5-phenylpyridineHCID 5360545SodiumHCID 184286505-Butylpyridin-2-amine

Produkt 1

HCID 1050975-Phenyl-2-pyridinamineAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-5-phenylpyridine (4.0 g., 0.021 mole) in dry diethyl ether (160 ml.) was added dropwise to a solution of sodium (3.39 g., 0.15 g-atom) in liquid ammonia (160 ml.) containing ferrous nitrate hexahydrate (0.095 g.). The resulting suspension was allowed to reflux for 4 hours. Ammonium chloride was added and the ammonia allowed to evaporate. The residue was treated with 5% aqueous sodium hydroxide (5 ml.). The mixture was filtered. The aqueous layer was extracted with ether (2 × 100 ml.). The combined ethereal layers were washed with brine and dried over sodium sulfate. The solution was concentrated and the residue recrystallized from methylcyclohexane. The product was triturated with chloroform (100 ml.). The mixture was filtered and the filtrate evaporated to give 2-amino-5-phenylpyridine (1.3 g., 36%), m.p. 133°-135° (lit. m.p. 133° in Chem. Ber., 91, 247 (1958).

Aufarbeitung

  1. temperatureto reflux for 4 hours
  2. customto evaporate
  3. additionThe residue was treated with 5% aqueous sodium hydroxide (5 ml.)
  4. filtrationThe mixture was filtered
  5. extractionThe aqueous layer was extracted with ether (2 × 100 ml.)
  6. washThe combined ethereal layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationThe solution was concentrated
  9. customthe residue recrystallized from methylcyclohexane
  10. customThe product was triturated with chloroform (100 ml.)
  11. filtrationThe mixture was filtered
  12. customthe filtrate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c2ab05e38d6f4460b569206306b25b0a
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04122274

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