Hydrochloric Acid → 3-Methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

HRID 880023Notes

Reaction equation

HRID 880023 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:15])[N:5]([CH3:14])[CH:6]=[CH:7][C:8]=1[C:9]([O:11]CC)=[O:10].Cl>C1COCC1.[Li+].[OH-]>[CH3:1][O:2][C:3]1[C:4](=[O:15])[N:5]([CH3:14])[CH:6]=[CH:7][C:8]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15122761Ethyl 3-methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 229377543-Methoxy-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 1 (2.2 g, 10 mmol) in THF (3 mL) was added LiOH (10.8 mg, 0.451 mmol) and the reaction mixture was stirred at rt for 16 h. The reaction mixture was acidified to pH=1 using HCl (1M aq., 12.50 mL, 12.50 mmol) concentrated and then evaporated to dryness to provide Intermediate 6 (1.9 g, 10 mmol, 100% yield) as a gray solid. HPLC/MS (Method D) RT=0.42 min, [M+1]+ 184. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.28 (1H, d, J=7.1 Hz), 5.97 (1H, d, J=6.6 Hz), 3.62 (3H, s), 3.31 (3H, s).

Workup

  1. concentrationconcentrated
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-e6ef3e98c74b460994b0857d54a03334
Source dataset
uspto-grants-2015_03
Patent number
US08993557B2

Reaction notes

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