p-Toluenesulfonic acid → HCID 70432961, compound

HRID 986243Notes

Reaction equation

HRID 986243 reaction equation
[CH3:1][CH:2]([C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5]CC)=O.[NH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl.C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][CH:2]1[C:3](=[O:5])[C:18]2[C:17](=[CH:26][CH:25]=[C:20]([C:21]([O:23][CH3:24])=[O:22])[CH:19]=2)[N:16]=[C:8]1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12082Methyl 4-aminobenzoateHCID 139166Propionic acid, 2-benzoyl-, ethyl ester

Product 1

HCID 70432961HCID 70432961, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7583Diphenyl EtherSolvent

Procedure

Ethyl alpha-methylbenzoylacetate (5 grams) and 3.67 grams of methyl p-aminobenzoate are dehydrated (by heating) for three days in 100 ml of chloroform in the presence of 0.7 gram of p-toluenesulfonic acid. p-Toluenesulfonic acid is removed therefrom, the filtrate is concentrated, and purified by silica gel column chromatography to give an oil. The resulting oily product is heated to reflux in 70 ml of diphenyl ether, cooled, and crystals which separate therefrom are collected by filtration and recrystallized from a mixture of dimethyl formamide and water to give 2 grams of methyl 3-methyl-2-phenyl-4-quinolone-6-carboxylate, colorless crystals, melting point above 300° C.

Workup

  1. customp-Toluenesulfonic acid is removed
  2. concentrationthe filtrate is concentrated
  3. custompurified by silica gel column chromatography
  4. customto give an oil
  5. temperatureThe resulting oily product is heated
  6. temperaturecooled
  7. customcrystals which separate
  8. filtrationtherefrom are collected by filtration
  9. customrecrystallized from a mixture of dimethyl formamide and water

Sources & evidence

ORD record
ord-1f427f43fd904877a26da0de847b3ab7
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

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