Hydrazine → 6-Chloro-3-hydrazinylpyridazine-4-carboxylic acid

HRID 521564Notes

Reaction equation

HRID 521564 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].[NH2:12][NH2:13]>CCO>[Cl:11][C:5]1[N:4]=[N:3][C:2]([NH:12][NH2:13])=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 4338043,6-Dichloropyridazine-4-carboxylic acid

Product 1

HCID 205385786-Chloro-3-hydrazinylpyridazine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3,6-dichloropyridazin-4-carboxylic acid (5 g, 26 mmol) in EtOH (200 mL) was added TEA (4 mL, 30 mmol) and hydrazine (5 mL, 80%). The reaction mixture was stirred at 85° C. for 3 hours. After cooled to room temperature, the mixture was concentrated in vacuum to give crude product 6-chloro-3-hydrazinylpyridazine-4-carboxylic acid (4.8 g), which was used for the next step directly without purification. LRMS (M+H+) m/z: calcd 189; found 189.

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture was concentrated in vacuum

Sources & evidence

ORD record
ord-ff16b08230e344ea9e4dcd518a6c019e
Source dataset
uspto-grants-2016_05
Patent number
US09328117B2

Reaction notes

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