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

HRID 2238834Notes

Reaction equation

HRID 2238834 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-a503ed07ef6f41eba717cf2d1df86b47
Source dataset
uspto-grants-2010_05
Patent number
US07718808B2

Reaction notes

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