4'-Methoxyacetophenone → HCID 59215170, compound

HRID 2244590Notes

Reaction equation

HRID 2244590 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-55a2c2138ad54776b50a0c82ecda8471
Source dataset
uspto-grants-2010_03
Patent number
US07678911B2

Reaction notes

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