Ethanol → 3-Amino-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

HRID 1073252

Reaktionsgleichung

Reaktionsgleichung von HRID 1073252
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[OH-].[Na+].Cl.[NH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=O.C([OH:33])C>O.O1CCCC1>[NH2:15][C:16]1[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[N:1][C:11]2[C:6]([C:4]=1[C:2]([OH:33])=[O:3])=[CH:7][CH:8]=[CH:9][CH:10]=2

Komponenten

7

Edukt 4

HCID 702EthanolHCID 7054Isatin2×HCID 14798Sodium HydroxideHCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

Produkt 1

HCID 150859463-Amino-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A 4.42 g portion of isatin was suspended in 25 ml of water in a three-necked 1 liter flask equipped with a reflux condenser and addition funnel. To this suspension was added a solution of 6.4 g of sodium hydroxide in 20 ml of water, then the mixture was heated to 90° C. A solution of 15.0 g of 2-amino-4'-phenylacetophenone, hydrochloride in 300 ml of a 50:50 mixture of ethanol:water was warmed slightly, then 100 ml of tetrahydrofuran was added to effect dissolution. This solution was added dropwise to the hot solution of isatin over 1.5 hours with vigorous stirring. When addition was complete, the solution was stirred at 90° C. for 1 hour and then the organic solvents were removed by distillation at 85° C. The remaining solution was cooled, filtered and the filtrate acidified to pH 5 with glacial acetic acid. The resulting solid was collected, washed with water and dried. The yellow solids were suspended in 40 ml of ethanol, filtered and dried, giving 2.19 g of the desired product, mp 223°-225° C. (dec.).

Aufarbeitung

  1. customequipped with a reflux condenser and addition funnel
  2. additionWhen addition
  3. customthe organic solvents were removed by distillation at 85° C
  4. temperatureThe remaining solution was cooled
  5. filtrationfiltered
  6. customThe resulting solid was collected
  7. washwashed with water
  8. customdried
  9. filtrationfiltered
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-208b9e45d46c47eab15f040892b6d5ef
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968702

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