Aniline → N-2-Pyridylaniline

HRID 1881034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881034
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:9]1([NH:8][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

8

Edukt 4

HCID 6115AnilineHCID 79732-BromopyridineHCID 8857Ethyl AcetateHCID 23676156Sodium t-butoxide

Produkt 1

HCID 81130N-2-PyridylanilineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 634876Binap, (A+-)-KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-bromopyridine (3.0 g) and aniline (5.3 g) were dissolved in toluene (40 mL), tris(dibenzylideneacetone)dipalladium (0) (350 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (480 mg) and sodium tert-butoxide (2.6 g) were added, then stirred at 80° C. for three hours. Ethyl acetate (100 mL) was added to the reaction solution, and then washed with water (100 mL). The organic layer was extracted with 2N hydrochloric acid (100 mL), and washed with ethyl acetate (100 mL). The water layer was made alkaline with 2N sodium hydroxide aqueous solution (150 mL) and then extracted with ethyl acetate (200 mL). The organic layer was washed with a saturated sodium chloride solution (50 mL). After drying on anhydrous sodium sulfate, filtration and vacuum concentration, the residue was washed with diethyl ether to give the above-identified compound (2.1 g, yield 72%).

Aufarbeitung

  1. washwashed with water (100 mL)
  2. extractionThe organic layer was extracted with 2N hydrochloric acid (100 mL)
  3. washwashed with ethyl acetate (100 mL)
  4. extractionextracted with ethyl acetate (200 mL)
  5. washThe organic layer was washed with a saturated sodium chloride solution (50 mL)
  6. dry with materialAfter drying on anhydrous sodium sulfate, filtration and vacuum concentration
  7. washthe residue was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0283c671889d4ec381d80ea07ab0abc3
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318781B2

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