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

HRID 1626325

Reaktionsgleichung

Reaktionsgleichung von HRID 1626325
[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

4

Edukt 2

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

Produkt 1

HCID 7766454-(Quinoline-8-sulfonamido)benzoic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

Ethyl 4-(quinoline-8-sulfonamido)benzoate (90, 10 g, 28.08 mmol) was dissolved in a mixture of THF-water (100:100 ml) and maintained at room temperature. To this solution was added LiOH (5.89 g, 14.0 mmol) and the resultant solution was refluxed overnight. The reaction mixture was then washed with ethyl acetate (3×50 ml) and then acidified with dilute HCl. The resultant suspension was filtered and residue was co-distilled with toluene. This product was then dried under vacuum to yield carboxylic acid 91 (8.28 g, 90%) as an off-white solid.

Aufarbeitung

  1. washThe reaction mixture was then washed with ethyl acetate (3×50 ml)
  2. filtrationThe resultant suspension was filtered
  3. customThis product was then dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f6d1d7d630fc4805bec109b7845bd3c3
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785450B2

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