Potassium Carbonate → 1-[2-Nitro-4'-(2-quinolinylmethoxy)-[1,1'-biphenyl]4-yl]ethanone

HRID 2380151노트

반응식

HRID 2380151 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[C:6]([N+:17]([O-:19])=[O:18])[CH:5]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Cl[CH2:45][C:46]1[CH:55]=[CH:54][C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]=1>CCCCCC.C(OCC)(=O)C.C(#N)C>[N+:17]([C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][C:7]=1[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:45][C:46]2[CH:55]=[CH:54][C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:47]=2)=[CH:14][CH:15]=1)([O-:19])=[O:18]

참가 물질

7

반응물 4

HCID 11430Potassium Carbonate2회HCID 203942-(Chloromethyl)quinoline2회HCID 2855718-Crown-62회HCID 189566144-Acetyl-4'-hydroxy-2-nitro biphenyl

생성물 1

HCID 99307361-[2-Nitro-4'-(2-quinolinylmethoxy)-[1,1'-biphenyl]4-yl]ethanone

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 21226206Ethyl acetate hexane용매

실험 절차

A mixture of the phenol (4.4 g, 17.12 mmole) of Step B, powdered anhydrous potassium carbonate (2.37 g, 17.12 mmole), 18-crown-6 (0.453 g, 1.71 mmole) and acetonitrile (38 mL) is stirred at room temperature under nitrogen for 15 minutes. 2-Chloromethylquinoline (3.34 g, 18.83 mmole, free base freshly prepared from the hydrochloride salt) is added and the mixture is refluxed for 10 hours. (TLC, 7:3 hexane-ethyl acetate). A 10% excess of potassium carbonate, 18-crown-6 and the chloromethylquinoline is added and reflux continued for another 4 hours. The solvent is removed and the residue is diluted with water and extracted with ethyl acetate (3x). The extracts are washed and dried (MgSO4). The residue is flash chromatographed (on silica Merck 60, preabsorbed in dichloromethane and eluted in order of increasing polarity with 7:3, 1:1 and 1:3 hexane-ethyl acetate followed by pure ethyl acetate) to provide the pure title compound (2.59 g). Recrystallization from toluene yields a yellow solid, m.p. 160°-162° C. (2.05 g, 30%).

후처리

  1. additionis added
  2. temperaturethe mixture is refluxed for 10 hours
  3. temperaturereflux
  4. waitcontinued for another 4 hours
  5. customThe solvent is removed
  6. additionthe residue is diluted with water
  7. extractionextracted with ethyl acetate (3x)
  8. washThe extracts are washed
  9. dry with materialdried (MgSO4)
  10. customchromatographed
  11. custom(on silica Merck 60, preabsorbed in dichloromethane and eluted in order of increasing polarity with 7:3, 1:1 and 1:3 hexane-ethyl acetate followed by pure ethyl acetate)

출처 및 근거

ORD 기록
ord-e132d570d4464ccc82ca6e36f677fd5e
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05364944

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