S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:20]=[CH:19][C:10]2[CH2:11][CH2:12][CH:13]([NH:17][CH3:18])[CH2:14][CH:15](O)[C:9]=2[CH:8]=1.O.[OH-].[Na+]>O1CCOCC1>[ClH:6].[Cl:6][C:7]1[CH:20]=[CH:19][C:10]2[CH2:11][CH2:12][CH:13]([NH:17][CH3:18])[CH:14]=[CH:15][C:9]=2[CH:8]=1
7.4 ml of concentrated sulfuric acid were added to a refluxing solution of 3.7 g of 3-chloro-5ξ-hydroxy-7-methylamino-6,7,8,9-tetrahydro [5H] benzocycloheptene in 37 ml of dioxane and the mixture was refluxed for 20 minutes and then was cooled to 20° C. 50 ml of water were added to the reaction mixture which was then made alkaline with sodium hydroxide. The mixture was extracted with methylene chloride and the organic extracts were washed with water, dried and evaporated to dryness. The resulting 3.5 g of product were dissolved in 5 ml of ethyl acetate and a solution of ethyl acetate saturated with hydrogen chloride was added thereto at 10° C. The mixture was vacuum filtered to obtain 3.3 g of 2-chloro-7-methylamino-6,7-dihydro [5H] benzocycloheptene hydrochloride melting at 195° C which was identical to the product of Example 10.
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