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

HRID 1017123

반응식

HRID 1017123 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b8e6a33ac8f043d6850272189f4a0645
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479436B1

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