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

HRID 1587570Notes

Reaction equation

HRID 1587570 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 (3×). 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 (3×)
  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-6b98af3f967648b7bea5d17fa983e144
Source dataset
uspto-grants-1993_06
Patent number
US05218124

Reaction notes

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