Hydrochloric Acid → 4-Chloro-5-(3-carboxymethyloxy-4-methoxybenzylamino)-3(2H)-pyridazinone

HRID 583109Notes

Reaction equation

HRID 583109 reaction equation
[Cl:1][C:2]1[C:3](=[O:29])[NH:4][N:5]=[CH:6][C:7]=1[N:8](OC=C=O)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12](N2CCN(C)CC2)[CH:11]=1.[OH-:30].[K+].[CH2:32]([OH:34])[CH3:33].Cl.[OH2:36]>>[Cl:1][C:2]1[C:3](=[O:29])[NH:4][N:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:34][CH2:32][C:33]([OH:36])=[O:30])[CH:11]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 86754293HCID 86754293, compound

Product 1

HCID 215841834-Chloro-5-(3-carboxymethyloxy-4-methoxybenzylamino)-3(2H)-pyridazinone

Procedure

A mixture comprising 0.3 g of 4-chloro-5-[3-(4-methylpiperazin-1-yl)-carbonylmethoxy-4-methoxybenzylamino]-3(2H)-pyridazinone, 2.0 g of potassium hydroxide, 10 ml of ethanol and 2 ml of water, was refluxed under heating with stirring overnight. The reaction solution was neutralized with an aqueous hydrochloric acid solution. Then, the solvent was distilled off under reduced pressure. Then, water was added to the obtained residue, and the mixture was extracted with chloroform. The extract solution was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 212 mg of the above-identified compound as white solid.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. additionThen, water was added to the obtained residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe extract solution was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-06d14136dc4a4006ac29f0ca7fd3839c
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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