Sodium Hydroxide → 6-Methyl-4-pyridazinecarboxylic acid hydrochloride

HRID 1880211Notes

Reaction equation

HRID 1880211 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([CH3:11])=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].[OH-].[Na+]>CO.[Pd]>[CH3:11][C:5]1[N:4]=[N:3][CH:2]=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 265992153-Chloro-6-methylpyridazine-4-carboxylic acid

Product 1

HCID 553007686-Methyl-4-pyridazinecarboxylic acid hydrochlorideYield 30.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3-chloro-6-methyl-pyridazine-4-carboxylic acid (500 mg, 2.89 mmol) in MeOH (50 mL) was added NaOH (395 mg, 9.85 mmol) in pellets, followed by 150 mg of Pd/C (10%). The reaction mixture was put under a H2 atmosphere for 3 hours (atmospheric pressure). The reaction mixture was filtered on celite, acidified with aq. HCl (pH=6), and concentrated under vacuo. Column chromatography (SiO2, CH2Cl2/MeOH 7/3) yielded 6-methyl-pyridazine-4-carboxylic acid (120 mg, 29%) as a brown solid.

Workup

  1. filtrationThe reaction mixture was filtered on celite
  2. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-21d3e6e20703469f9e332bca55fef9ee
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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