1,2-Dimethoxyethane → 5-Phenyl-2-pyridinamine

HRID 251774

Reaktionsgleichung

Reaktionsgleichung von HRID 251774
[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.COCCOC.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.C(OCC)(=O)C>[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

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 706222-Amino-5-bromopyridine

Produkt 1

HCID 1050975-Phenyl-2-pyridinamineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Dissolving 5.0 g (29 mmol) of 2-amino-5-bromopyridine, 3.6 g (30 mmol) of phenylboronic acid and 0.67 g of tetrakis (triphenylphosphine) palladium into 90 milliliter of 1,2-dimethoxyethane, adding 45 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 6 hours. After completion of the reaction, the resultant solution was further dissolved into ethyl acetate, filtering the solution, washing with water, dried with the use of sodium sulfate. Removing the solvent by distillation, 4.0 g of crude 5-phenyl-2-amino-pyridine was obtained.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ac2cfa47963f4b0595baf8829a9520da
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07867629B2

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