4'-Methoxyacetophenone → HCID 59215170, compound

HRID 2252312Notes

Reaction equation

HRID 2252312 reaction equation
[Na].[CH3:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].Cl[C:14]1[N:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CCO>[Cl:23][C:21]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([CH2:2][C:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)=[O:4])[N:22]=1

Participants

6

Reactant 3

HCID 74764'-MethoxyacetophenoneHCID 8540472,6-Dichloronicotinic acidHCID 5360545Sodium2×

Product 1

HCID 59215170HCID 59215170, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 702EthanolSolvent

Procedure

Elemental sodium (173 mg, 7.5 mmol) was added to 40 mL of absolute EtOH stirring under nitrogen. After all of the sodium reacted, 4-methoxyacetophenone (1.44 g, 7.5 mmol) was added, and the reaction stirred an additional 15 minutes. 2,6-Dichloronicotinic acid (1 g, 5.2 mmol) and copper acetate (80 mg, 0.65 mmol) was added and the reaction was stirred at reflux for 16 hours. The reaction was cooled to room temperature and quenched with 1 mL concentrated acetic acid. The mixture was concentrated to a solid, and redissolved in EtOAc. A small portion of fine inorganic precipitate was filtered off. The organic layer was extracted with 3×100 mL 1N NaOH. This was acidified with 1 N HCl to a pH of ˜4. A precipitate formed and was collected by vacuum filtration, yielding 6-chloro-2-[2-(4-methoxyphenyl)-2-oxo-ethyl]-nicotinic acid (1 g, 63%) as a tan solid.

Workup

  1. stirringthe reaction was stirred
  2. temperatureat reflux for 16 hours
  3. customquenched with 1 mL concentrated acetic acid
  4. concentrationThe mixture was concentrated to a solid
  5. dissolutionredissolved in EtOAc
  6. filtrationA small portion of fine inorganic precipitate was filtered off
  7. extractionThe organic layer was extracted with 3×100 mL 1N NaOH
  8. customA precipitate formed
  9. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-a2af84dc8f6f46b49a62abd4b88102ac
Source dataset
uspto-grants-2008_01
Patent number
US07321041B2

Reaction notes

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