p-Toluenesulfonic acid → HCID 70432956, compound

HRID 986245Notes

Reaction equation

HRID 986245 reaction equation
[C:1]([CH2:9][C:10](OCC)=[O:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([O:24][CH2:25][CH3:26])(=[O:23])[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH2:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:2]1([C:1]2[CH2:9][C:10](=[O:11])[C:19]3[C:17](=[C:16]([C:15]([O:24][CH2:25][CH3:26])=[O:23])[CH:22]=[CH:21][CH:20]=3)[N:18]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6877Ethyl 2-aminobenzoateHCID 7170Ethyl benzoylacetate

Product 1

HCID 70432956HCID 70432956, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 7 grams of ethyl benzoylacetate, 6 grams of ethyl anthranilate and 0.5 gram of p-toluenesulfonic acid is dehydrated (by heating) in 300 ml of benzene for three days. Benzene is evaporated therefrom, and the resulting oil is heated at 250° to 280° C. for 0.5 hour in 20 ml of diphenyl ether. After cooling, 250 ml of n-hexane is added thereto, and crystals which separate out therefrom are collected by filtration and recrystallized from methanol to give 4.2 grams of ethyl 2-phenyl-4-quinolone-8-carboxylate, pale brown needles, melting point 218° to 219° C.

Workup

  1. customBenzene is evaporated
  2. temperaturethe resulting oil is heated at 250° to 280° C. for 0.5 hour in 20 ml of diphenyl ether
  3. temperatureAfter cooling
  4. addition250 ml of n-hexane is added
  5. customcrystals which separate out
  6. filtrationtherefrom are collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-34484fd9f0ae4d5d9e04cae63fc5ca00
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

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