[Mg].[I-].[CH:3]1(Br)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[NH2:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#N.Cl.[OH-:20].[Na+]>O1CCCC1.C(OCC)C>[CH:3]1([C:13]([C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[NH2:10])=[O:20])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]13.1 g of magnesium turnings, 10 ml of ethyl ether and several pieces of iodide were placed in a flask under a nitrogen gas, and the mixture was refluxed to fade out the color caused by iodide. 90 ml of an ethyl ether solution containing 20 g of cyclohexyl bromide was added dropwise over a 30-minute period under reflux with stirring. The temperature of the reaction solution was returned to room temperature, 40 ml of a tetrahydrofuran solution containing 4.8 g of 2-aminobenzonitrile was added dropwise over a 30-minute period, and the mixture was stirred for 30 minutes. 150 ml of an aqueous 1N hydrochloric acid solution was cautiously added, and the mixture was neutralized with a dilute aqueous sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1) and recrystallized from ethyl acetate-n-hexane to give 6.2 g of 2-cyclohexylcarbonylaniline.
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