Sodium Hydroxide → 3-Amino-2-[1,1'-biphenyl]-4-yl-6-trifluoromethyl-4-quinolinecarboxylic acid

HRID 1073269Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073269
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=O.Cl.[NH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)=O.[OH-:33].[Na+]>O.C(O)C.O1CCCC1>[NH2:17][C:18]1[C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)=[N:8][C:9]2[C:5]([C:6]=1[C:7]([OH:33])=[O:12])=[CH:4][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:11][CH:10]=2

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 123514965-(trifluoromethyl)-2,3-dihydro-1H-indole-2,3-dioneHCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

Produkt 1

HCID 150859573-Amino-2-[1,1'-biphenyl]-4-yl-6-trifluoromethyl-4-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6.45 g of 5-trifluoromethylisatin (J. Org. Chem., 1344, 42, 1977) in 70 ml of 2.5N sodium hydroxide at 90°-95° C. was added a warm solution of 10.55 g of 2-amino-4'-phenylacetophenone, hydrochloride in 75 ml of water, 75 ml of ethanol and 50 ml of tetrahydrofuran over 30 minutes. The mixture was refluxed 1.5 hours, then the organic solvents were boiled off, the mixture diluted with 125 ml of water and filtered while still warm. The recovered solid was dissolved in 500 ml of hot water and filtered twice through celite. The second filtrate was acidified to pH 5 with glacial acetic acid, heated to near boiling, then cooled and the solid collected. This solid was recrystallized from acetonitrile/tetrahydrofuran, giving 5.74 g of the desired product as green crystals mp 255°-260° C. (dec.).

Aufarbeitung

  1. temperatureThe mixture was refluxed 1.5 hours
  2. filtrationfiltered
  3. temperaturewhile still warm
  4. dissolutionThe recovered solid was dissolved in 500 ml of hot water
  5. filtrationfiltered twice through celite
  6. temperatureheated
  7. temperaturecooled
  8. customthe solid collected
  9. customThis solid was recrystallized from acetonitrile/tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-1781b3bd005c4bec817f22a2ff5fb777
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968702

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