Sodium Hydroxide → 3-Amino-2-[1,1'-biphenyl]-4-yl-6,8-dichloro-4-quinolinecarboxylic acid

HRID 1073260

Reaktionsgleichung

Reaktionsgleichung von HRID 1073260
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[NH:7][C:6](=[O:12])[C:5]2=O.[OH-:14].[Na+].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>O.C(O)C.O.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:7][C:8]2[C:4]([C:5]=1[C:6]([OH:12])=[O:14])=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=2[Cl:11]

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 807715,7-Dichloro-1H-indole-2,3-dione2×HCID 124871822-Amino-1-((1,1'-biphenyl)-4-yl)ethan-1-one hydrochloride

Produkt 1

HCID 150859543-Amino-2-[1,1'-biphenyl]-4-yl-6,8-dichloro-4-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittelHCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A 3.02 g portion of 5,7-dichloroisatin was suspended in 25 ml of water in a 500 ml three-necked flask. A solution of 3.96 g of sodium hydroxide in 15 ml of water was added and the mixture heated to 90° C. A 6.0 g portion of 2-amino-4'-phenylacetophenone hydrochloride was dissolved in a mixture of 80 ml of absolute ethanol:water (1:1) and 20 ml of tetrahydrofuran. This solution was kept warm and with stirring, added dropwise to the 5,7-dichloroisatin solution over 1.5 hours. The resulting solution was refluxed 1.5 hours, then the solvent was distilled off at 85° C. The red solids were collected and washed with 50 ml of water. These solids were then stirred in 1800 ml of water, filtered and the filtrate acidified to pH 5 with glacial acetic acid. The resulting orange solids were collected and dried, giving 3.25 g of the desired product, mp 244°-245° C.

Aufarbeitung

  1. temperatureThis solution was kept warm
  2. temperatureThe resulting solution was refluxed 1.5 hours
  3. distillationthe solvent was distilled off at 85° C
  4. customThe red solids were collected
  5. washwashed with 50 ml of water
  6. stirringThese solids were then stirred in 1800 ml of water
  7. filtrationfiltered
  8. customThe resulting orange solids were collected
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4a06145db81d475e8aa07e4e275fb0b4
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968702

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