Pyridazine-4-carboxylic Acid → 3-Methylpyridazine-4-carboxylic acid

HRID 550528

Reaction equation

HRID 550528 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=[O:8])=[CH:3][N:2]=1.CO.[CH2:12](Cl)Cl>>[CH3:12][C:3]1[N:2]=[N:1][CH:6]=[CH:5][C:4]=1[C:7]([OH:9])=[O:8]

Participants

3

Reactant 2

HCID 2761046Pyridazine-4-carboxylic AcidHCID 21226129Dichloromethane methanol

Product 1

HCID 534147303-Methylpyridazine-4-carboxylic acid

Procedure

To a solution of 4-pyridazinecarboxylic acid (490 mg, 3.9 mmol) in MeOH/DCM (20/10 ml) was added at 0° C. trimethylsilildiazomethane (25.5 mmol). The solution was warm at r.t. and stirred overnight. Volatiles were evaporated in vacuo, the crude dissolved in DCM, washed with NaHCO3 satured and dried over Na2SO4. After filtration and concentration to dryness in vacuo, the crude was purified by column chromatography (DCM:MeOH=98 to 2) to give 400 mg of the title compound.

Workup

  1. customVolatiles were evaporated in vacuo
  2. dissolutionthe crude dissolved in DCM
  3. washwashed with NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration to dryness in vacuo
  6. customthe crude was purified by column chromatography (DCM:MeOH=98 to 2)

Sources & evidence

ORD record
ord-3350765f503146e58941656a0524ca59
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Linked notes

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