[CH:1]([NH:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[CH:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2)=O.[H-].[Al+3].[H-].[H-].[H-].[OH-].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>C(O)(C)C.O.C(OCC)(=O)C.CCOCC>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[CH3:1][NH:3][CH2:4][CH:5]1[C:6]2[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=2[CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2
5-Formamidomethyl-5H-dibenzo[a,d]cycloheptene (3.80 g., 0.015 mole), dissolved in 400 ml. of absolute ether is added gradually to a solution oflithium aluminum hydride (0.87 g., 0.023 mole) in 45 ml. of absolute ether at a rate such that gentle refluxing is maintained. The reaction mixture, containing a precipitate, is heated to refluxing with stirring for 26 hours. After cooling to room temperature, 10 ml. of ethyl acetate is addedto decompose the excess hydride. Water, 1 ml., 15% sodium hydroxide, 1 ml. and water, 3 ml. then are added to the vigorously stirred reaction mixture. After standing several days, the reaction mixture is filtered andthe solid washed several times by suspension in ether. The combined filtrates and ether washings are evaporated on a film evaporator under reduced pressure, the pale yellow oily residue is dissolved in dilute hydrochloric acid, the solution extracted with ether to remove non-basic material, then rendered alkaline and the product extracted with ether. After washing with water and drying over anhydrous sodium sulfate, the ether is evaporated on a film evaporator under reduced pressure. The yellow oily residue weighs 3.05 g. A 2.95 g. portion is dissolved in isopropyl alcohol and a solution of 1.60 g. (0.0138 mole) of maleic acid in 5 ml. of isopropyl alcohol is added. The hydrogen maleate salt of the product separates out in white crystals. It melts at 163°-164° C. (clears, 165° C.) after further recrystallization from isopropyl alcohol and drying in vacuo over phosphorus pentoxide.
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