Lithium Hydroxide → 4-(Quinoline-8-sulfonamido)benzoic acid

HRID 1626328

Reaktionsgleichung

Reaktionsgleichung von HRID 1626328
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 1357549Ethyl 4-(quinoline-8-sulfonamido)benzoate

Produkt 1

HCID 7766454-(Quinoline-8-sulfonamido)benzoic acidAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of sulfonamide 90 (34 gm, 95.5 mmol) in THF and water (1:1), LiOH (20 gm, 47.66 mmol) was added and the resulting mixture was allowed to stir at 80° C. overnight. After completion of reaction, the crude mixture was washed with EtOAc. The aqueous layer was acidified with citric acid and filtered. Thus obtained solid was washed with Et2O and azeotroped by toluene, under reduced pressure to afford acid 91 (30 gm, 95.8% yield) which was taken forward for the next step without further purification.

Aufarbeitung

  1. customAfter completion of reaction
  2. washthe crude mixture was washed with EtOAc
  3. filtrationfiltered
  4. washThus obtained solid was washed with Et2O
  5. customazeotroped by toluene, under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e20a7dfbba42489db805e9108a695cc2
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785450B2

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