Acetone Cyanohydrin → 2-(5-Nitroquinolin-8-yl)carbonylcyclohexane-1,3-dione

HRID 1017123

Reaktionsgleichung

Reaktionsgleichung von HRID 1017123
[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2].[C:17]1(=[O:24])[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18]1.C1(N=C=NC2CCCCC2)CCCCC1.CC(C)(O)C#N.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(N(CC)CC)C>[N+:1]([C:4]1[CH:13]=[CH:12][C:11]([C:14]([CH:18]2[C:19](=[O:23])[CH2:20][CH2:21][CH2:22][C:17]2=[O:24])=[O:16])=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)([O-:3])=[O:2]

Komponenten

8

Edukt 5

HCID 6406Acetone CyanohydrinHCID 10340Sodium CarbonateHCID 104341,3-CyclohexanedioneHCID 10868DicyclohexylcarbodiimideHCID 154053315-Nitroquinoline-8-carboxylic acid

Produkt 1

HCID 154053322-(5-Nitroquinolin-8-yl)carbonylcyclohexane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

1.0 g of 5-nitro-8-quinolinecarboxylic acid together with 0.5 g of 1,3-cyclohexanedione and 1.0 g of dicyclohexylcarbodiimide were stirred in 15 ml of acetonitrile at room temperature for about 12 hours. 0.7 g of triethylamine and 0.2 ml of acetone cyanohydrin were then added. After 4 hours, the reaction solution was poured into aqueous sodium carbonate solution and extracted with ethyl acetate. The aqueous phase was acidified with hydrochloric acid and extracted with ethyl acetate. The organic phase was dried, the solvent was distilled off and the residue was chromatographed over silica gel.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. distillationthe solvent was distilled off
  5. customthe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b8e6a33ac8f043d6850272189f4a0645
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479436B1

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