Methanol → Methyl 2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1662010Notes

Reaction equation

HRID 1662010 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:16]O>C1(C)C=CC=CC=1>[O:1]=[C:2]1[C:3]([C:4]([O:6][CH3:16])=[O:5])=[CH:7][CH:8]=[CH:9][NH:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178418543HCID 178418543, compound

Product 1

HCID 579028Methyl 2-oxo-1,2-dihydropyridine-3-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a flask is added 2-hydroxynicotinic acid (10 g, 72 mmol), concentrated H2SO4 (2 mL) and MeOH (400 mL), followed by toluene (80 mL). The reaction mixture is heated to reflux overnight with a Dean-Stark trap. After cooling to RT, the mixture is filtered and the filtrate is concentrated. The residue is dissolved in DCM (200 mL), neutralized with saturated aqueous NaHCO3 to pH 7 and extracted with DCM (200 mL) for three times. The combined organic phases are dried and concentrated to give the desired product (8.2 g, 74% yield). MS (m/z): 153.9 (M+H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight with a Dean-Stark trap
  3. filtrationthe mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. dissolutionThe residue is dissolved in DCM (200 mL)
  6. extractionextracted with DCM (200 mL) for three times
  7. customThe combined organic phases are dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c06b5664a2f4fe692540c73ef64e64b
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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