5-ethyl-2,3-dihydro-1H-indole-2,3-dione → 3-Amino-2-[1.1'-biphenyl]-4-yl-6-ethyl-4-quinolinecarboxylic acid

HRID 1073261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073261
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=O.[CH2:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[C:23]2=O)[CH3:19].C([OH:33])C.O>O1CCCC1>[NH2:2][C:3]1[C:4]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)=[N:25][C:26]2[C:22]([C:23]=1[C:24]([OH:29])=[O:33])=[CH:21][C:20]([CH2:18][CH3:19])=[CH:28][CH:27]=2

Komponenten

5

Edukt 3

HCID 5834875-ethyl-2,3-dihydro-1H-indole-2,3-dioneHCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochlorideHCID 19096565Water ethanol

Produkt 1

HCID 150859553-Amino-2-[1.1'-biphenyl]-4-yl-6-ethyl-4-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 12.63 g portion of 2-amino-4'-phenylacetophenone, hydrochloride was dissolved in a mixture of 168 ml of absolute ethanol:water (1:1) and 40 ml of tetrahydrofuran. This solution was kept warm and with stirring, added dropwise to the 5-ethylisatin solution over 2 hours. The mixture was refluxed for 2 hours, then the solvent was distilled off at 85° C. and the reaction cooled for 1 hour. The red solids were collected, stirred with 2 liters of water for 1.5 hours and then filtered. The filtrate was acidified to pH 5 with glacial acetic acid. The resulting yellow solids were collected and dried, giving 4.47 g of the desired product, mp 240°-241° C.

Aufarbeitung

  1. temperatureThis solution was kept warm
  2. temperatureThe mixture was refluxed for 2 hours
  3. distillationthe solvent was distilled off at 85° C.
  4. temperaturethe reaction cooled for 1 hour
  5. customThe red solids were collected
  6. stirringstirred with 2 liters of water for 1.5 hours
  7. filtrationfiltered
  8. customThe resulting yellow solids were collected
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5f39dcef84324f5898bc47ca80540ecc
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968702

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