Methyl 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate → 1-Methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

HRID 626186Notes

Reaction equation

HRID 626186 reaction equation
[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10]C)=[O:9])=[CH:4][C:3]1=[O:12]>CO.O>[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]1=[O:12]

Participants

4

Reactant 1

HCID 819408Methyl 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 8199231-Methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate (1 g, 1.0 eq) in 25 mL MeOH was added a solution of LiOHH2O (755 mg, 3.0 eq) in 5 mL water at rt. The reaction was then stirred at rt for 2 h. Then the solvent was removed in vacuo, and water was added to the residue, followed by addition of 3N HCl (aq) to adjust pH=1˜3. The product was collected by filtration and washed with water to give the product as white solid (540 mg, 60% yield). 1H NMR (400 MHz, DMSO-d6) δ 13.56 (brs, 1H), 7.80 (d, J=7.2 Hz, 1H), 6.83 (d, J=1.6 Hz, 1H), 6.53 (d, J=6.8 Hz, 1.6 Hz, 1H), 3.46 (s, 3H).

Workup

  1. customThen the solvent was removed in vacuo, and water
  2. additionwas added to the residue
  3. additionfollowed by addition of 3N HCl (aq)
  4. filtrationThe product was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-a1120d430b0940b1be6b99641f1b39fa
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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