1,3-Dibromopropane → Ciclazindol
Reaction equation
Cl.[NH2:2][C:3]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.Br[CH2:21][CH2:22][CH2:23]Br>C(O)C>[Cl:19][C:15]1[CH:14]=[C:13]([C:11]2([OH:12])[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]3[CH2:21][CH2:22][CH2:23][N:2]=[C:3]23)[CH:18]=[CH:17][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-Amino-3-(m-chlorophenyl)-3H-indol-3-ol hydrochloride (2.3 g) is converted to its oily base then heated under reflux in ethanol (10 ml) with 1,3-dibromopropane (1.55 g) for 20 hours. On cooling the title compound is obtained as its hydrobromide, m.p. 270°-273°C (decomp.).
Workup
- temperaturethen heated