Hydrochloric Acid → 1-Methyl-2-oxo-1,2-dihydropyridine-4-carbaldehyde

HRID 1186415Notes

Reaction equation

[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([CH:8](OCC)[O:9]CC)=[CH:4][C:3]1=[O:15].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][N:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][C:3]1=[O:15]

Participants

Conditions

Temperature: 50 °C

Procedure

1-Methyl-4-(diethoxymethyl)-2(1H)-pyridone (1.20 g, 5.58 mmol) was dissolved in tetrahydrofuran (10.0 mL). To this, 1 mol/L hydrochloric acid (10.0 mL) was added under a nitrogen atmosphere at room temperature and the mixture was stirred at 50° C. for 6 hours. By addition of a saturated aqueous sodium bicarbonate solution to neutralize the reaction mixture, the reaction was stopped. Then, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=9/1) to give 1-methyl-4-formyl-2(1H)-pyridone (717 mg, yield: 95%).

Workup

extractionThen, extraction with ethyl acetate
washby washing with brine
dry with materialdrying over anhydrous sodium sulfate
customThe solvent was evaporated off under reduced pressure
customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record: ord-d2ff345608c641d19a19c1f40567cbe9
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673908B2

Reaction notes

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