Hydrochloric Acid → Methyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylate

HRID 422808Notes

Reaction equation

HRID 422808 reaction equation
[Cl:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1.Cl.[CH3:14]COC(C)=O>CO>[Cl:1][C:2]1[C:3]([C:10]([O:12][CH3:14])=[O:11])=[N:4][N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 666741324-Chloro-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

Product 1

HCID 57886211Methyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylateYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-chloro-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (390 mg, 2.07 mmol) and conc. HCl (0.10 mL) in MeOH (6 mL) was refluxed for 8 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to give the crude material that was redissolved into EtOAc. The organic layer was washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that was purified by silica gel flash column chromatography (100% hexanes to 10 to 20 to 30 to 50% EtOAc in hexanes) to afford 72 mg (17%) of the desired product.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give the crude material that
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude material that
  8. customwas purified by silica gel flash column chromatography (100% hexanes to 10 to 20 to 30 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5bf7c72c96054de0b99e95185020bacf
Source dataset
uspto-grants-2012_01
Patent number
US08101639B2

Reaction notes

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