p-Toluenesulfonic acid → HCID 70432961, 화합물

HRID 986243노트

반응식

HRID 986243 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 70432961HCID 70432961, 화합물수율 28.1%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 7583Diphenyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1f427f43fd904877a26da0de847b3ab7
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04711898

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