Triethylamine → Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 422753Notes

Reaction equation

HRID 422753 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[C:18](O)=[CH:17][C:16](=[O:20])[N:15]([CH3:21])[CH:14]=1)=[O:12])[CH3:9].O=P(Cl)(Cl)[Cl:24]>>[CH2:8]([O:10][C:11]([C:13]1[C:18]([Cl:24])=[CH:17][C:16](=[O:20])[N:15]([CH3:21])[CH:14]=1)=[O:12])[CH3:9]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 54685351Ethyl 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 11615451Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylateYield 67%

Procedure

Triethylamine (7.07 mL, 50.7 mmol) was added to a suspension of 4-hydroxy-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (10.0 g, 50.7 mmol) and POCl3 (27.85 mL, 304.3 mmol). After stirring 16 hours, the reaction mixture was concentrated under reduced pressure. The resulting residue was poured onto ice, carefully neutralized with saturated K2CO3 solution, and diluted with EtOAc. The layers were separated and the aqueous phase further extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to yield 7.3 g (67%) clean desired product.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe resulting residue was poured onto ice
  3. additiondiluted with EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous phase further extracted with EtOAc
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da377c1ef3254a5da209872999502156
Source dataset
uspto-grants-2012_01
Patent number
US08101639B2

Reaction notes

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