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

HRID 1366091Notes

Reaction equation

HRID 1366091 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 7%

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 (7%) 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-a66a2bcbec7d4bf382ec887238dca554
Source dataset
uspto-grants-2011_02
Patent number
US07893065B2

Reaction notes

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