Sodium Hydroxide → HCID 53492322, Verbindung

HRID 1801365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1801365
[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]2[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([O:28]C)=[O:27])[CH:20]=3)[NH:15]2)[CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O1CCCC1>[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]2[C:23]([CH3:24])([CH3:25])[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:26]([OH:28])=[O:27])[CH:20]=3)[NH:15]2)[CH:11]=[CH:12][CH:13]=1)(=[O:6])=[O:7])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67442053HCID 67442053, Verbindung

Produkt 1

HCID 53492322HCID 53492322, VerbindungAusbeute 28,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 2-(3-(N-isopropylsulfamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (120 mg, 0.288 mmol) in methanol/tetrahydrofuran (4 mL/4 mL) was added 1N sodium hydroxide (4.32 mL). The resultant mixture was heated to reflux for 1.5 h. Organic solvent was removed and the residue was dissolved in water. The aqueous layer was acidified to pH=4. The precipitates were filtered, and redissolved in tetrahydrofuran, dried over anhydrous magnesium sulfate. anhydrous magnesium sulfate was removed, and after evaporation, the residue was treated with dichloromethane to afford 33 mg of 2-(3-(N-isopropylsulfamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (Yield: 28%). MS (ESI+APCI) M+1=403.1.

Aufarbeitung

  1. temperatureto reflux for 1.5 h
  2. customOrganic solvent was removed
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe precipitates were filtered
  5. dissolutionredissolved in tetrahydrofuran
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customanhydrous magnesium sulfate was removed
  8. customafter evaporation
  9. additionthe residue was treated with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e6d633ffb06e415f8e8674b61717045b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344137B2

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