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

HRID 1971151Notes

Reaction equation

HRID 1971151 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

Triethyl amine (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-4378582d27884ea4b557a033111d0ece
Source dataset
uspto-grants-2013_04
Patent number
US08431574B2

Reaction notes

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