Ethanol → 3-Amino-2-[1,1'-biphenyl]-4-yl-6-bromo-4-quinolinecarboxylic acid

HRID 1073253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073253
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-].[Na+].Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)=O.C([OH:34])C>O.O1CCCC1>[NH2:16][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)=[N:7][C:8]2[C:4]([C:5]=1[C:6]([OH:11])=[O:34])=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2

Komponenten

7

Edukt 4

HCID 702EthanolHCID 68895-Bromoisatin2×HCID 14798Sodium HydroxideHCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

Produkt 1

HCID 150859473-Amino-2-[1,1'-biphenyl]-4-yl-6-bromo-4-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A 5.0 g portion of 5-bromoisatin was suspended in 25 ml of water in a three-necked 1 liter flask equipped with a reflux oondenser and addition funnel. A solution of 4.36 g of sodium hydroxide in 20 ml of water was added and the mixture heated to 90° C. A solution of 9.9 g of 2-amino-4'-phenylacetophenone hydrochloride in 200 ml of a 50:50 mixture of ethanol:water was warmed slightly, then 100 ml of tetrahydrofuran was added to effect solution. This solution was added dropwise to the hot 5-bromoisatin solution over 1.5 hours with vigorous stirring. When addition was complete, the mixture was stirred at 90° C. for 1 hour, then the organic solvents were removed by distillation at 85° C. The solution was cooled and the red solids collected, washed with water and saved. The red solid saved above was suspended in 1 liter of water, stirred for 1 hour and then filtered. The filtrate was acidified to pH 5 with glacial acetic acid and the resulting yellow solids collected and washed with water. The second crop was pure giving 3.80 g of the desired product, mp 239°-240° C. (dec.).

Aufarbeitung

  1. customequipped with a reflux oondenser and addition funnel
  2. additionWhen addition
  3. customthe organic solvents were removed by distillation at 85° C
  4. temperatureThe solution was cooled
  5. customthe red solids collected
  6. washwashed with water
  7. stirringstirred for 1 hour
  8. filtrationfiltered
  9. customthe resulting yellow solids collected
  10. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-9406a1ae537c4d5d9ef31eadd6e56897
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968702

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