Hydrochloric Acid → 4,6-Dichloro-3-pyridazinecarboxylic acid

HRID 558223Notes

Reaction equation

HRID 558223 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([O:11]C)=[O:10].[Li+].[OH-].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 17848322Methyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 219192804,6-Dichloro-3-pyridazinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4,6-dichloro-pyridazine-3-carboxylate (6.01 g, 29.03 mmol, WO 2004/031174) in THF (29 ml) at 0° C. is added 29 ml of aqueous 1.0 M LiOH with stirring. The resulted mixture is stirred continuously at 0° C. for 40 min and monitored by TLC. The reaction mixture is diluted with water, and acidified to pH 1-2 with aqueous 1.0 M HCl. The crude product is suspended between the organic and aqueous layers. After filtration and washed with water and hexane, and dried under vacuum, the product is obtained.

Workup

  1. stirringThe resulted mixture is stirred continuously at 0° C. for 40 min
  2. filtrationAfter filtration
  3. washwashed with water and hexane
  4. customdried under vacuum
  5. customthe product is obtained

Sources & evidence

ORD record
ord-e6e2288296e240a09d4bc6acf64c9c84
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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