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

HRID 1497417

Reaktionsgleichung

Reaktionsgleichung von HRID 1497417
[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 VII (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 VIII (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-3d3ba294e8974c5cb88ce4b01e100753
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199968B2

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