Potassium Carbonate → Ethyl 4-(2-oxopyridin-1(2H)-yl)benzoate

HRID 1604596

Reaction equation

HRID 1604596 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.I[C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 142891Ethyl 4-iodobenzoateHCID 178516071HCID 178516071, compound

Product 1

HCID 16656197Ethyl 4-(2-oxopyridin-1(2H)-yl)benzoateYield 35.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 2-hydroxypryidine (2.40 g), ethyl 4-iodobenzoate (6.97 g), potassium carbonate (3.83 g) and copper (253 mg) in N,N-dimethylformamide (12 ml) was stirred for 4 hours at 175° C. under nitrogen atmosphere. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. To the residue was added ethyl acetate and 1N hydrochloric acid, the organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo to give ethyl 4-(2-oxo-1,2-dihydropyridin-1yl)benzoate (2.18 g) as brown powder.

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionTo the residue was added ethyl acetate and 1N hydrochloric acid
  4. washthe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b125ecb2f76d44a0ab4f641ee0c30925
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Linked notes

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