Sodium Hydroxide → HCID 58476143, Verbindung

HRID 2045672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045672
[CH3:1][N:2]([CH3:28])[S:3]([C:6]1[CH:7]=[C:8]([CH:12]2[C:21]([CH3:23])([CH3:22])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:24]([O:26]C)=[O:25])[CH:18]=3)[NH:13]2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].[OH-].[Na+]>CO.O1CCCC1>[CH3:28][N:2]([CH3:1])[S:3]([C:6]1[CH:7]=[C:8]([CH:12]2[C:21]([CH3:23])([CH3:22])[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:24]([OH:26])=[O:25])[CH:18]=3)[NH:13]2)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67440754HCID 67440754, Verbindung

Produkt 1

HCID 58476143HCID 58476143, VerbindungAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 2-(3-(N,N-dimethylsulfamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (149 mg, 0.37 mmol) in methanol/tetrahydrofuran (5 mL/5 mL) was added 1N sodium hydroxide (5.6 mL). The resultant mixture was heated to reflux for 2.5 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 dissolved in tetrahydrofuran, dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed, and after evaporation, the residue was treated with ethyl acetate to afford 29 mg of 2-(3-(N,N-dimethylsulfamoyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid. (Yield: 20%). MS (ESI+APCI) M+1=389.1.

Aufarbeitung

  1. temperatureto reflux for 2.5 h
  2. customOrganic solvent was removed
  3. dissolutionthe residue was dissolved in water
  4. filtrationThe precipitates were filtered
  5. dissolutiondissolved 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 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f33f265b59c749dfafa35af289f6ee61
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586747B2

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