Sodium Carbonate → 5-Phenyl-2-pyridinamine

HRID 251779

Reaktionsgleichung

Reaktionsgleichung von HRID 251779
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[C:9]1([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 706222-Amino-5-bromopyridine

Produkt 1

HCID 1050975-Phenyl-2-pyridinamineAusbeute 113,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Dissolving 5.5 g (32 mmol) of 2-amino-5-bromopyridine, 4.3 g (32 mmol) of phenylboronic acid and 0.80 g of tetrakis (triphenylphosphine) palladium into 100 milliliter of 1,2-dimethoxyethane, adding 50 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 8 hours. After completion of the reaction and after filtration of the solution, washing the organic layer with water, dried it with the use of sodium sulfate. Removing the solvent by distillation, 6.2 g of crude 5-phenyl-2-amino-pyridine was obtained.

Aufarbeitung

  1. temperatureunder heating for 8 hours
  2. customAfter completion of the reaction
  3. filtrationafter filtration of the solution
  4. washwashing the organic layer with water
  5. dry with materialdried it with the use of sodium sulfate
  6. customRemoving the solvent
  7. distillationby distillation

Quellen und Nachweise

ORD-Eintrag
ord-ec9a1cc466e646a2a696f9652a37ef15
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07867629B2

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