4-Bromophenylhydrazine hydrochloride → 5-bromo-3-(2-phthalimidoethyl)-1H-indole

반응식

C(O[CH:4](OCC)[CH2:5][CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])C.Cl.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30]N)=[CH:26][CH:25]=1>C(O)(=O)C.O>[Br:23][C:24]1[CH:25]=[C:26]2[C:27](=[CH:28][CH:29]=1)[NH:30][CH:4]=[C:5]2[CH2:6][CH2:7][N:8]1[C:9](=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]1=[O:17]

참가 물질

실험 절차

4-[1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl]butanal diethyl acetal (11.6 g) was added with vigorous stirring to a solution of 4-bromophenylhydrazine hydrochloride (9.0 g) in 50% aqueous acetic acid (370 ml). The mixture was heated on a steam bath for 4 hours and was then diluted with water, while still hot, to 1 l. The mixture was cooled and an orange yellow precipitate was filtered off and dried in vacuo. The solid was boiled in ethanol (250 ml) for 1 hour and residual solid filtered off and dried to afford the title compound as a yellow solid (9.5 g) m.p. 206°-209° C. Crystallisation of a portion of this solid (0.5 g) from ethanol (25 ml) gave a sample (0.25 g) m.p. 208°-212° C.