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

HRID 45313

Reaction equation

HRID 45313 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)[CH3:2].[OH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.N>[O:13]=[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]1[C:8]1[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:12])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22043Ethyl 4-bromobenzoateHCID 178516071HCID 178516071, compound

Product 1

HCID 16656197Ethyl 4-(2-oxopyridin-1(2H)-yl)benzoateYield 86%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 222AmmoniaSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromobenzoic acid ethyl ester (4.58 g, 20.00 mmol), 2-hydroxypyridine (0.95 g, 10.00 mmol), potassium carbonate (1.39 g, 10.00 mmol), and CuI (0.095 g, 0.50 mmol) was stirred at 120° C. for 6 h under a nitrogen atmosphere. The diluted aqueous ammonia (50 mL) was added, and the solution was extracted with ethyl acetate (3×50 mL). The organic extracts were dried over anhydrous sodium sulfate, filtered. The solvent was removed in vacuo to afford ethyl 4-(2-oxopyridin-1(2H)-yl)benzoate in 86% yield (2.10 g); NMR (CDCl3, 300 MHz) δ 8.15 (d, J=8.5 Hz, 2H), 7.46 (d, J=8.5 Hz, 2H), 7.39 (ddd, J=2.0, 6.6, 9.0 Hz, 1H), 7.31 (dd, J=2.0, 6.6 Hz, 1H), 6.65 (d, J=9.0 Hz, 1H), 6.26 (dt, J=1.1, 6.6 Hz, 1H), 4.38 (q, J=7.1 Hz, 2H), 1.39 (t, J=7.1 Hz, 3H).

Workup

  1. extractionthe solution was extracted with ethyl acetate (3×50 mL)
  2. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f9350cf1b1f9479faa377d6b002e2b01
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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