Water → Methyl 3-acetyl-2-pyridinecarboxylate

HRID 2372222Notes

Reaction equation

HRID 2372222 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])=[O:4].[Cl-].[NH4+].O.[C:17](OCC)(=O)C>>[C:7]([C:6]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])[CH3:17]

Participants

5

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 13239660Methyl 3-(chlorocarbonyl)pyridine-2-carboxylate

Product 1

HCID 15257078Methyl 3-acetyl-2-pyridinecarboxylate

Procedure

Lithium methylsulfonylmethyl(methyl)cuprate(I) is chilled to -78°, and 2-methoxycarbonylnicotinoyl chloride (3.2 g, 16.0 mmol) is slowly added, keeping the temperature at -65° to -70°. The mixture is stirred at -78° for 1 hour, after which aq. ammonium chloride is added. The mixture is warmed to RT, poured into water and ethyl acetate and extracted with ethyl acetate. The combined organic phases are dried and reduced and the product is purified by prep. TLC to give methyl 3-acetyl-2-pyridinecarboxylate.

Workup

  1. customat -65° to -70°
  2. extractionextracted with ethyl acetate
  3. customThe combined organic phases are dried
  4. customthe product is purified by prep

Sources & evidence

ORD record
ord-d83f53894d8c46e196a5c718e7927b6e
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Reaction notes

Loading…