Acetyl chloride → Methyl 2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 2202988Notes

Reaction equation

HRID 2202988 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[C:11](Cl)(=O)C>CO>[O:1]=[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][NH:3]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178524562HCID 178524562, compound

Product 1

HCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-hydroxypyridine-4-carboxylic acid (5.0 g) in MeOH (50 ml) was added acetyl chloride (26 ml) dropwise at 0° C. over 15 min. The reaction mixture was slowly warmed to room temperature, and stirred for 20 h. The reaction mixture was concentrated in vacuo, and diluted with EtOAc and water. The organic layer was washed with saturated NaHCO3 solution, concentrated in vacuo, and purified by column chromatography (MeOH/DCM) to afford the title compound (3.5 g) as an off-white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc and water
  3. washThe organic layer was washed with saturated NaHCO3 solution
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-51ce1b92ccd846349737e743ca32fe74
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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