Anisole → Methyl 6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 337539Notes

Reaction equation

HRID 337539 reaction equation
COC1C=CC(C[O:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=2)=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[O:8]=[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][NH:10]1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 23144104Methyl 6-(4-methoxybenzyloxy)nicotinate

Product 1

HCID 416343Methyl 6-oxo-1,6-dihydropyridine-3-carboxylateYield 89.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Methyl 6-(4-methoxybenzyloxy)nicotinate (2.66 g, 9.73 mmol) obtained in Step 2 and anisole (10.6 mL) were dissolved in trifluoroacetic acid (15 mL), followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and saturated sodium hydrogencarbonate was added to the resulting residue, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The precipitated solid was collected by filtration to afford methyl 2-oxo-1,2-dihydropyridine-5-carboxylate (1.33 g, 89%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated sodium hydrogencarbonate
  2. additionwas added to the resulting residue
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-58d15164297c4b9f9c7a1a40758478d9
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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