Water → HCID 15917442, compound

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[CH2:6][C:7]3([O:26][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:10][N:9](C(OC1C=CC=CC=1)=O)[CH2:8]3.[OH-].[K+].O>C(O)CC>[ClH:1].[Cl:1][C:2]1[CH:28]=[CH:27][C:5]2[CH2:6][C:7]3([O:26][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:10][NH:9][CH2:8]3

Participants

Procedure

A mixture of 6-chloro-2'-phenoxycarbonylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (25.0 g), potassium hydroxide (25 g) and water (25 ml) in n-propanol (250 ml) is heated under reflux for four hours. Removal of the solvent under reduced pressure yields a solid which is stirred with water (500 ml) and extracted with ether. The combined ether extract is washed with 3 N hydrochloric acid and basified with saturated sodium carbonate solution. The material which separates is extracted with ether, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent is removed to yield product as a solid (13.5 g, 78%). A 4.0 g-portion of the solid is dissolved in ether and converted to the product hydrochloride salt (4.3 g). An analytical sample is twice recrystallized from ethyl acetate/methanol, mp 238°-239° (dec).