Hydrazine hydrate (1:1) → 4-chloro-N-(6-(hydrazinecarbonyl)pyridin-2-yl)picolinamide

HRID 2178600

Reaktionsgleichung

Reaktionsgleichung von HRID 2178600
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=2)=[O:13])[N:6]=1)=O.O.[NH2:22][NH2:23]>C(O)C>[Cl:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([C:12]([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([NH:22][NH2:23])=[O:2])[N:6]=2)=[O:13])[CH:19]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 668487256-[(4-Chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester

Produkt 1

HCID 581030194-chloro-N-(6-(hydrazinecarbonyl)pyridin-2-yl)picolinamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The crude 6-[(4-chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester from the previous step (25.3 g, 87.8 mmol) was suspended in ethanol (200 mL), and hydrazine hydrate (21.3 mL, 439 mmol) was added. The reaction mixture was refluxed for 4 hours, solvent removed under reduced pressure, and the residue suspended in acetonitrile and collected by filtration. The solids were washed with acetonitrile (2×100 mL) and diethylether (2×100 mL), and dried under reduced pressure to afford 25.3 g (92% yield) of 4-chloro-N-(6-(hydrazinecarbonyl)pyridin-2-yl)picolinamide as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customsolvent removed under reduced pressure
  3. filtrationcollected by filtration
  4. washThe solids were washed with acetonitrile (2×100 mL) and diethylether (2×100 mL)
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c21df8faeca9485cbb56c4076a2721da
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067933B2

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