HCID 12721727, compound → HCID 23284540, compound

HRID 368981Notes

Reaction equation

HRID 368981 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([CH2:7][C:8]([NH2:10])=[O:9])=[O:6].C(O[CH:17](OCC)[CH2:18][C:19](=O)[CH2:20][CH3:21])C>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([C:7]1[C:8](=[O:9])[NH:10][C:19]([CH2:20][CH3:21])=[CH:18][CH:17]=1)=[O:6]

Participants

4

Reactant 2

HCID 12721727HCID 12721727, compoundHCID 16729434HCID 16729434, compound

Product 1

HCID 23284540HCID 23284540, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

α-(3-Chlorobenzoyl)acetamide (19.76 g, 0.1 mol) was dissolved in 250 ml of ethanol, and the solution was mixed with 19.15 g (0.11 mol) of 1,1-diethoxy-3-pentanone and heated under reflux for 40 hours. After cooling to room temperature, the reaction solution was poured into ice water and extracted with chloroform. The organic layer was washed with 1 N hydrochloric acid, brine and dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and then the resulting filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was mixed with diethyl ether and the thus formed crystals were collected by filtration and washed with diethyl ether to give 18.50 g of 3-(3-chlorobenzoyl)-6-ethyl-2-pyridone in the form of crystals. The yield was 71%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 40 hours
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with 1 N hydrochloric acid, brine
  5. dry with materialdried over anhydrous magnesium sulfate, magnesium sulfate
  6. customwas removed by filtration
  7. concentrationthe resulting filtrate was concentrated under a reduced pressure
  8. additionThereafter, the resulting residue was mixed with diethyl ether
  9. filtrationthe thus formed crystals were collected by filtration
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f5493466778744a694b380fcfc5b6594
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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