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

HRID 2380151Notes

Reaction equation

HRID 2380151 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-e132d570d4464ccc82ca6e36f677fd5e
Source dataset
uspto-grants-1994_11
Patent number
US05364944

Reaction notes

Loading…