Hydrochloric Acid → 1-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 1676331Notes

Reaction equation

HRID 1676331 reaction equation
[Li+].[OH-].[CH3:3][N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([O:12]C)=[O:11])[C:5]1=[O:14].Cl>C1COCC1.CO>[CH3:3][N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([OH:12])=[O:11])[C:5]1=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 819366Methyl 1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 12015101-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 44.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

LiOH (1.3 mL, 1.3 mmol, 1.0 M) was added to a solution of methyl 1-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate (0.11 g, 0.65 mmol) in a mixture of THF-MeOH (3:1 ratio, 8 mL) at room temperature. After stirring for 2 hours, 1 N HCl (1.3 mL) was added. The reaction mixture was extracted with EtOAc, dried over MgSO4, and concentrated to give the desired product (0.044 g, 44% for 2 step process). 1H NMR (400 MHz, CD3OD) δ 8.45 (dd, 1H), 8.06 (dd, 1H), 6.66 (t, 1H), 3.71 (s, 3H).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-01103b31696046afae62520197fc890d
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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