Pyridine → 6-Phenyl-2-pyridone

HRID 399703

Reaction equation

HRID 399703 reaction equation
ClCC([O:5][CH2:6][CH3:7])=O.[N:8]1C=CC=CC=1.Cl.CN(C)[CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.C([O-])(=O)C.[NH4+]>C(O)C>[C:21]1([C:19]2[NH:8][C:6](=[O:5])[CH:7]=[CH:17][CH:18]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7751Ethyl chloroacetateHCID 928441-Propanone, 3-(dimethylamino)-1-phenyl-, hydrochloride (1:1)HCID 517165Ammonium Acetate

Product 1

HCID 878896-Phenyl-2-pyridone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-chloroacetate (10.6 ml, 0.1 mol) is slowly added to hot (105° C.) pyridine (8.9 ml, 0.11 mmol whereby the temperature is maintained in the range of 100° C. to 110° C. The resulting brown oil is dissolve in ethanol (60 ml), β-dimethylamino propiophenone hydrochloride (17.7 g, 0.1 mol; prepared to according to Example 1) and ammonium acetate (60 g) are added and the mixture is boiled under reflux for 4 h. After cooling, the mixture is filtered and the solvent is evaporated in vacuo. The residue is crystallized from water, collected by filtration and purified by re-crystallization from toluene. The title compound is obtained as colorless crystals (4.7 g, 28% of th.) with mp 200° C.

Workup

  1. temperatureis maintained in the range of 100° C. to 110° C
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered
  5. customthe solvent is evaporated in vacuo
  6. customThe residue is crystallized from water
  7. filtrationcollected by filtration
  8. custompurified by re-crystallization from toluene

Sources & evidence

ORD record
ord-a0559b7ee1f84e8f9903c886bbb5e917
Source dataset
uspto-grants-1998_10
Patent number
US05824624

Linked notes

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