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Hydrochloric Acid → 6-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid

HRID 1894963
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1894963
[C:1]1([S:7]([N:10](S(C2C=CC=CC=2)(=O)=O)[C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([O:23]C)=[O:22])=[CH:14]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].O.Cl>CO.CN(C)C=O>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[N:17]=[CH:16][C:15]([C:21]([OH:23])=[O:22])=[CH:14]3)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67002239Methyl 6-[bis(phenylsulfonyl)amino]quinoline-3-carboxylate

Produkt 1

HCID 670023616-[(Phenylsulfonyl)amino]quinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 6-[bis(phenylsulfonyl)amino]quinoline-3-carboxylate (0.29 g, 0.601 mmol) in methanol (2.4 mL) was added a 1 M solution of sodium hydroxide in H2O (2.4 mL, 2.4 mmol). N,N-dimethylformamide (1 mL) was added to aid solubility and the resulting suspension was stirred at room temperature for 48 h. The reaction was then warmed to 60° C. and stirred for 96 h. A solution of hydrochloric acid (1.0 M in water) was added until pH=7. The mixture was extracted with ethyl acetate three times. The extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure and used as obtained (Int-12, 0.201 g, 61%). LC-MS: (FA) ES+ 329.

Aufarbeitung

  1. temperatureThe reaction was then warmed to 60° C.
  2. stirringstirred for 96 h
  3. extractionThe mixture was extracted with ethyl acetate three times
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customas obtained (Int-12, 0.201 g, 61%)

Quellen und Nachweise

ORD-Eintrag
ord-c4dbde8d252b4dc185051571131428cf
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08513421B2

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