Oxalyl chloride → Methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 2243891Notes

Reaction equation

HRID 2243891 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9]([OH:11])=[O:10])=[CH:3]1.[C:12](Cl)(=O)C(Cl)=O>ClCCl>[CH3:12][O:10][C:9]([C:4]1[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=1)=[O:11]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 592704N(1)-methyl-2-pyridone-5-carboxylic acid

Product 1

HCID 597449Methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylateYield 56.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture obtained in Example 26 (˜2.5 g total) was dissolved in dichloromethane (30 mL). Oxalyl chloride (2 M in dichloromethane, 16.3 mL. 32.6 mmol) was added and the reaction was stirred for 30 min. The reaction was quenched with methanol, then diluted with dichloromethane and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated, then chromatographed in 20-50% ethyl acetate in hexanes to yield the title product 1.55 g, 26% (2 steps).

Workup

  1. customThe reaction was quenched with methanol
  2. additiondiluted with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed in 20-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1769e2a8f51540439c1db6a2df7e14fe
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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