[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH:6]=[CH:7]OC.[C:13]1([NH:19]N)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.[Cl-].[Na+]>C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:19][CH:7]=2)[CH:10]=[CH:11][CH:12]=1A 90 g portion of the abovementioned methyl (3-methoxystyryl) ether was dissolved in 100 ml of ethanol. Then the solution was added dropwise to a mixed solution of 59.3 g phenylhydrazine, 800 ml ethanol and 53 ml concentrated hydrochloric acid under reflux, and after the addition, reflux heating was continued for 2 more hours. The reaction mixture was then cooled to room temperature, and after adding water, sodium chloride and a small amount of ethyl acetate, the mixture was stirred and the precipitated crystals were collected by filtration. The crystals were dissolved in chloroform and washed with dilute hydrochloric acid and sodium bicarbonate aqueous solution. And the solution was dried and concentrated to obtain a residue. Then toluene was added to the residue, and after refluxed for one hour. After cooling, precipitated crystals were then collected by filtration to obtain 89.6 g of 3-(3-methoxyphenyl)indole.
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