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

HRID 1040237Notes

Reaction equation

HRID 1040237 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f7d5a17d7a274b35ba78a4cd2bcbbcad
Source dataset
uspto-grants-2013_10
Patent number
US08552196B2

Reaction notes

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