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

HRID 1017123

Reaction equation

HRID 1017123 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b8e6a33ac8f043d6850272189f4a0645
Source dataset
uspto-grants-2002_11
Patent number
US06479436B1

Linked notes

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