Dimethylformamide → Methyl 1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 1630740Notes

Reaction equation

HRID 1630740 reaction equation
CO[CH:3]=[C:4]([C:11]([O:13][CH3:14])=[O:12])/[CH:5]=[CH:6]\[C:7]([O:9]C)=O.CN(C=O)C.[F:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1>O>[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[C:7](=[O:9])[CH:6]=[CH:5][C:4]([C:11]([O:13][CH3:14])=[O:12])=[CH:3]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 97314-FluoroanilineHCID 86657760HCID 86657760, compound

Product 1

HCID 26986032Methyl 1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 mL round-bottomed flask was charged with (Z)-dimethyl 4-(methoxymethylene)pent-2-enedioate (2.70 g, 13.5 mmol) and 50 mL of DMF. 4-fluorobenzenamine (1.43 ml, 14.8 mmol) was added dropwise at rt. After stirring at rt for 15 min, the yellow mixture was heated to reflux overnight. The reaction was then diluted with water (200 mL) and extracted with ether (3×100 mL). The combined extracts were dried with MgSO4 and concentrated to give a solid. Purification by MPLC gave methyl 1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridine-3-carboxylate as a slightly yellow solid.

Workup

  1. temperaturethe yellow mixture was heated
  2. temperatureto reflux overnight
  3. extractionextracted with ether (3×100 mL)
  4. dry with materialThe combined extracts were dried with MgSO4
  5. concentrationconcentrated
  6. customto give a solid
  7. customPurification by MPLC

Sources & evidence

ORD record
ord-283373eee3cd417c90972f0831e211df
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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