Nitrogen → 2-Acetamido-5-aminopyridine

HRID 865673

Reaktionsgleichung

Reaktionsgleichung von HRID 865673
N#N.[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][N:8]=1)(=[O:5])[CH3:4].C([O-])=O.[NH4+]>CN(C=O)C.[Pd].CO>[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][N:8]=1)(=[O:5])[CH3:4]

Komponenten

7

Edukt 3

HCID 947NitrogenHCID 3451252-Acetamido-5-nitropyridineHCID 2723923Ammonium formate

Produkt 1

HCID 27352192-Acetamido-5-aminopyridineAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A N2 covered solution of 1.19 g (6.6 mmol) of the product from Step 1 in 24 ml of DMF was treated with 2.07 g (32.9 mmol) of ammonium formate followed by 0.36 g of palladium on carbon catalyst. After stirring vigorously at room temperature for 17 hours, the reaction was diluted with MeOH and the catalyst was removed by filtration through celite. The filtrate was concentrated in vacuo and the residue was chromatographed over silica gel (3% MeOH: 0.3% NH4OH: CH2Cl2) to yield 0.876 g, m.p. 152°-153.5° C. (88.2%) of the titled product.

Aufarbeitung

  1. customthe catalyst was removed by filtration through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was chromatographed over silica gel (3% MeOH: 0.3% NH4OH: CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-96c5e8a930fb438ebc8d061ffae6a959
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05567722

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