Methanol → 1-isopropyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

HRID 1479756Notes

Reaction equation

HRID 1479756 reaction equation
[CH:1]([N:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12]C)=[O:11])=[CH:6][C:5]1=[O:14])([CH3:3])[CH3:2].[OH-].[Li+].O1CCCC1.CO>O>[CH:1]([N:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:12])=[O:11])=[CH:6][C:5]1=[O:14])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58550769HCID 58550769, compound

Product 1

HCID 446007331-isopropyl-2-oxo-1,2-dihydropyridine-4-carboxylic acidYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 1-isopropyl-2-oxo-1,2-dihydropyridine-4-carboxylate (70 mg, 0.36 mmol), lithium hydroxide (57.1 mg, 1.36 mmol), tetrahydrofuran (50 mL), methanol (10 mL) and water (10 mL) was stirred at 20° C. for 4 hours. The mixture was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give 1-isopropyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (50 mg, 72%) as a white solid. LRMS (M+H+) m/z: calcd 181.07. found 181.

Workup

  1. customThe mixture was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1be844e256d64e9ab493f997e1617e9f
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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