[O:1]=[C:2]1[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][NH:3]1)=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[C:10]=3[Cl:18].[OH-:19].[K+].Cl>C(O)C.O>[NH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[C:10]([Cl:18])[C:11]([Cl:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C:7]=1[C:2]([OH:19])=[O:1]
The above lactam was hydrolyzed with base according to the following procedure: 5 g of 1-oxo-6-methoxy-7,8-dichloro-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole were dissolved in a mixture of 77 ml of ethanol and 51 ml of water. 13.9 g of potassium hydroxide were added, and the solution was heated to refluxing temperature overnight under a nitrogen atmosphere. The reaction mixture was cooled, and the pH adjusted to about 4 by the addition of 12N aqueous hydrochloric acid. A precipitate formed in the acidic solution, which precipitate was isolated by filtration, and the filter cake washed with water. 5.15 g of 3-(2-aminoethyl)-5-methoxy-6,7-dichloroindol-2-carboxylic acid were obtained. The compound melted at 248°-249° C.
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