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

HRID 2380151ノート

反応式

HRID 2380151 の反応式
[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]

参加物

7

反応物 4

HCID 11430Potassium Carbonate2 回HCID 203942-(Chloromethyl)quinoline2 回HCID 2855718-Crown-62 回HCID 189566144-Acetyl-4'-hydroxy-2-nitro biphenyl

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-e132d570d4464ccc82ca6e36f677fd5e
出典データセット
uspto-grants-1994_11
特許番号
US05364944

反応ノート

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