تفاعل #2467333

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 (3x)
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 (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%).

المصدر