[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[Li].BrC1C=CC=CN=1.C([Li])CCC.[CH3:20][O:21][C:22]1[CH:38]=[CH:37][C:25]([C:26]([NH:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]=[O:32])=[O:27])=[CH:24][CH:23]=1>O1CCCC1.CCCCCC.CCOCC>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([NH:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]([OH:32])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:27])=[CH:37][CH:38]=1Pyridyl lithium, prepared by adding 2-bromopyridine (30.0 g., 0.19 mole) in 200 ml. of ether to 131 ml. of a hexane solution of 1.6 molar n-butyl lithium (0.2 mole) at -70°C., is added in 25 min. to a solution of o-(4-methoxybenzamido)benzaldehyde (8.6 g., 0.035 mole) in 300 ml. of tetrahydrofuran at -25°C. over a 20 min. period with stirring. Stirring is continued for 20 min. at -25°C. 1 hr. at -10°C. and then at 0°C. for 30 min. The reaction mixture is poured into 1500 ml. of cold 1N hydrochloric acid, the aqueous layer separated, washed with ethyl acetate, made strongly basic with concentrated ammonium hydroxide and extracted with ethyl acetate. The ethyl acetate extract is washed with water, brine, dried over sodium sulfate and concentrated and the residue thus obtained triturated with ether to provide a 46% yield of 4-methoxy-2'-[hydroxy(2-pyridyl)methyl]benzanilide, m.p. 127.5°-128.5°C. (corr.).
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