Hydrazine hydrate (1:1) → HCID 70104763, compound

HRID 840551Notes

Reaction equation

HRID 840551 reaction equation
C(OC(C1N=[N:8][C:9]([O:12][C:13]2[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:10]C=1)=O)C.[OH2:20].[NH2:21][NH2:22]>C(O)C>[CH3:19][C:14]1[C:13]([O:12][CH:9]2[NH:8][CH2:13][CH:14]([C:19]([NH:21][NH2:22])=[O:20])[NH:15][CH2:10]2)=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 544471436-(2-Methylpyridin-3-yloxy)pyridazine-3-carboxylic acid ethyl ester

Product 1

HCID 70104763HCID 70104763, compoundYield 121.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

6-(2-Methylpyridin-3-yloxy)-pyridazine-3-carboxylic acid ethyl ester (D11) (1.07 g, 4.13 mmol) and hydrazine monohydrate (0.23 ml, 7.22 mmol) in ethanol (100 ml) was stirred at room temperature for 1 hour then heated at 50° C. for 1 hour and finally heated at reflux for 4 hours. A second portion of hydrazine monohydrate (0.23 ml, 7.22 mmol) was added and the mixture refluxed for a further 2 hours. After being allowed to cool the solvent was removed in vacuo. The off-white solid residue was subjected to column chromatography using 25% MeOH/EtOAc as eluant, resulting in a white crystalline product (0.63 g, 62%).

Workup

  1. temperaturefinally heated
  2. temperatureat reflux for 4 hours
  3. temperaturethe mixture refluxed for a further 2 hours
  4. temperatureto cool the solvent
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-9b9e682308ba4a1e9164d6f3275bbc0c
Source dataset
uspto-grants-2002_04
Patent number
US06369060B1

Reaction notes

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