Hydrochloric Acid → HCID 72210863, compound

HRID 1244247Notes

Reaction equation

HRID 1244247 reaction equation
C[O-].[Na+].[CH3:4][O:5][C:6]([C:8]1[N:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1Cl)=[O:7].Cl.[C:17]([O-])(O)=[O:18].[Na+]>C1COCC1.CCOC(C)=O>[CH3:4][O:5][C:6]([C:8]1[N:9]=[N:10][C:11]([Cl:15])=[CH:12][C:13]=1[O:18][CH3:17])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 17848322Methyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 72210863HCID 72210863, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium methoxide (25 wt % I methanol, 1.1 mL) is added to a stirred solution of 4,6-dichloro-pyridazine-3-carboxylic acid methyl ester (1.03 g, 5 mmol) in THF (25 mL) cooled to 0° C. The reaction mixture is stirred at room temperature overnight and then poured into 1N HCl (8 mL). The resulting solution is then neutralized by saturated NaHCO3. EtOAc (20 mL) is added and the layers are separated. The aqueous layer is extracted twice with EtOAc (20 mL) and the combined extracts are washed with brine (25 mL), dried (Na2SO4) and evaporated. The residue is then purified by flash column chromatography (silica gel, eluted with 2:1 Hexane:EtOAc) to give 6-chloro-4-methoxy-pyridazine-3-carboxylic acid methyl ester as a white solid.

Workup

  1. customthe layers are separated
  2. extractionThe aqueous layer is extracted twice with EtOAc (20 mL)
  3. washthe combined extracts are washed with brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue is then purified by flash column chromatography (silica gel, eluted with 2:1 Hexane:EtOAc)

Sources & evidence

ORD record
ord-6c27b114b86244ed8343777de3166f66
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

Loading…