Hydrochloric Acid → 4-(3,4-dichlorophenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinone

HRID 884336Notes

Reaction equation

HRID 884336 reaction equation
O.C(O)(O)C.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[C:15](=[O:23])[N:16]([CH3:22])[N:17]=[CH:18][C:19]=2[O:20]C)[CH:10]=[CH:11][C:12]=1[Cl:13].[OH-].[K+].Cl>O>[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[C:15](=[O:23])[N:16]([CH3:22])[N:17]=[CH:18][C:19]=2[OH:20])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 668430824-(3,4-dichlorophenyl)-5-methoxy-2-methyl-2H-pyridazin-3-oneHCID 86643495Water ethanediol

Product 1

HCID 674269854-(3,4-dichlorophenyl)-5-hydroxy-2-methyl-3(2H)-pyridazinoneYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 ml of water/ethanediol (1:1) were added to 1.0 g (7.4 mmol) of 4-(3,4-dichlorophenyl)-5-methoxy-2-methyl-2H-pyridazin-3-one and 0.4 g of potassium hydroxide (2 eq), and the mixture was reacted at 150° C. overnight. The reaction mixture was added to 50 ml of water and adjusted to pH 1 using concentrated hydrochloric acid, and the resulting precipitate was filtered off. Recrystallization from isopropanol gave 0.2 g of pure product.

Workup

  1. customthe mixture was reacted at 150° C. overnight
  2. filtrationthe resulting precipitate was filtered off
  3. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-44e857b43afd423a97709fba21ef8f18
Source dataset
uspto-grants-2012_08
Patent number
US08242055B2

Reaction notes

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