Hydrochloric Acid → 1-[2-(p-Carboxyphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole

反応式

C([O:3][C:4]([C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH3:22])=[C:14]2[N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH3:22])=[C:14]2[N:23]2[CH:27]=[CH:26][N:25]=[CH:24]2)=[CH:28][CH:29]=1)([OH:5])=[O:3]

参加物

実験手順

A solution of 1-[2-(p-ethoxycarbonylphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole (1.66 g) and 3N sodium hydroxide (20 ml) in absolute ethanol (20 ml) is stirred and refluxed for 2 hours. The solution is cooled and acidified to pH 3 with 3N hydrochlorid acid. The precipitate which forms (m.p.>300°) is collected. This solid is dissolved in a saturated sodium bicarbonate solution and the carboxylic acid is reprecipitated by acidifying the solution to pH 5 with 3N hydrochloric acid. The white solid is collected to give 1-[2-(p-carboxyphenoxy)-ethyl]-2-(1-imidazolyl)-3-methylindole; NMR (DMSO): δ2.17 (s, 3H), 4.30 (m, 4H).