p-Toluenesulfonic acid → Methyl 2-phenyl-4-quinolone-6-carboxylate

HRID 986236Notes

Reaction equation

HRID 986236 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]([CH2:20][C:21](OCC)=[O:22])(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[C:13]1([C:12]2[CH2:20][C:21](=[O:22])[C:3]3[C:2](=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:4]=3)[N:1]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7170Ethyl benzoylacetateHCID 12082Methyl 4-aminobenzoate

Product 1

HCID 70432662Methyl 2-phenyl-4-quinolone-6-carboxylateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
255 °C

Procedure

Methyl p-aminobenzoate (3.0 grams) and 4.1 grams of ethyl benzoylacetate are dissolved in 100 ml of chloroform and the solution is subjected to azeotropic dehydration for two days after the addition of 0.5 gram of p-toluenesulfonic acid. Chloroform is evaporated therefrom, n-hexane is added to the residue, the extract with n-hexane is evaporated, 30 ml of diphenyl ether is added to the residue, the mixture is heated at 255° C. for twenty minutes, cooled, crystals separate out therefrom are collected by filtration, washed with n-hexane and dried to give 4.4 grams of methyl 2-phenyl-4-quinolone-6-carboxylate, needles, melting at higher than 300° C.

Workup

  1. customChloroform is evaporated
  2. additionn-hexane is added to the residue
  3. extractionthe extract with n-hexane
  4. customis evaporated
  5. addition30 ml of diphenyl ether is added to the residue
  6. temperaturecooled
  7. customcrystals separate out
  8. filtrationtherefrom are collected by filtration
  9. washwashed with n-hexane
  10. customdried

Sources & evidence

ORD record
ord-c905e5f26b184991ba40580ab8a1f785
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

Loading…