تفاعل #1674752

معادلة التفاعل

potassium carbonate

18-crown-6

chloromethylquinoline

phenol

4-Acetyl-4'-hydroxy-2-nitro biphenyl

2-Chloromethylquinoline

18-crown-6

potassium carbonate

→

title compound

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

المذيبات

acetonitrile

hexane ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONis added
2. 2
   درجة الحرارةthe mixture is refluxed for 10 hours
3. 3
   درجة الحرارةreflux
4. 4
   workup.WAITcontinued for another 4 hours
5. 5
   أخرىThe solvent is removed
6. 6
   workup.ADDITIONthe residue is diluted with water
7. 7
   استخلاصextracted with ethyl acetate (3×)
8. 8
   غسيلThe extracts are washed
9. 9
   تجفيفdried (MgSO4)
10. 10
    أخرىchromatographed
11. 11
    أخرى(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)

الإجراء التجريبي

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%).

المصدر