Methanol → Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 8808Notes

Reaction equation

HRID 8808 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=[O:14])[C:11]([C:15]([OH:17])=[O:16])=[CH:10][C:9]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1.S(=O)(=O)(O)O.[CH3:30]O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=[O:14])[C:11]([C:15]([O:17][CH3:30])=[O:16])=[CH:10][C:9]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 219848936-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 21984816Methyl 6-(2-chlorophenyl)-5-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

Procedure

A 250 mL rb flask equipped with a magnetic stir bar was charged with 6.68 g (19.0 mmol) of the product of Step A, 100 mL methanol, 3 mL of concentrated sulfuric acid and the suspension was refluxed overnight. The resulting clear solution was then cooled to room temperature and evaporated. The residue was partitioned between EtOAc and 5% aqueous Na2CO3 and separated. The organic layer was washed with water, brine, dried (MgSO4), filtered and evaporated to afford the title compound.

Workup

  1. customA 250 mL rb flask equipped with a magnetic stir bar
  2. temperaturethe suspension was refluxed overnight
  3. customevaporated
  4. customThe residue was partitioned between EtOAc and 5% aqueous Na2CO3
  5. customseparated
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-29f404ef857d4408835b46d31710774a
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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