Tetrahydrofuran → 3-Pyridinecarboxylic acid, 2-(4-methoxybenzoyl)-

HRID 861325Notes

Reaction equation

HRID 861325 reaction equation
C1COCC1.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([O:14][C:15](=[O:16])[C:7]=12)=[O:13].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Mg]Br)=[CH:21][CH:20]=1.[NH4+].[Cl-]>Cl>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:15]([C:7]2[C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=[CH:11][N:6]=2)=[O:16])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 178491912HCID 178491912, compound

Product 1

HCID 113343683-Pyridinecarboxylic acid, 2-(4-methoxybenzoyl)-Yield 27.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a THF (15 ml) solution of pyridine-2,3-dicarboxylic acid anhydride (1.0 g, 6.7 mmol) was added dropwise a THF solution of 4-methoxyphenylmagnesium bromide (0.89M, 8.0 ml, 7.1 mmol) at -78° C. The reaction mixture was stirred at the same temperature for 1 h and then a saturated aqueous solution of NH4Cl (20 ml) was added to quench the reaction. The reaction mixture was diluted with 1N HCl and extracted with AcOEt. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (E. Merck, Kieselgel 60/chloroform:methanol=10:1) to give 2-(4-methoxyphenylcarbonyl)-3-pyridine carboxylic acid (479 mg) as a colorless solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionextracted with AcOEt
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (E. Merck, Kieselgel 60/chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-5b0711e903ae4287bcd8c0853656fca6
Source dataset
uspto-grants-1998_02
Patent number
US05714479

Reaction notes

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