2',4'-Dichloroacetophenone → 5-chloro-2-(2,4-dichlorophenyl)-1H-indole
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11])=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19]N)=[CH:15][CH:14]=1>O>[Cl:12][C:13]1[CH:14]=[C:15]2[C:16](=[CH:17][CH:18]=1)[NH:19][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11])=[CH:1]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2,4-dichloroacetophenone (378 mg, 2.0 mmol), p-chloro-phenylhydrazine (358 mg, 2.0 mmol and polyphosphoric acid (PPA) (0.5 mL) is heated at 100° C. for 8 h, cooled to room temperature, diluted with water, stirred briefly, allowed to stand at room temperature for 16 h and filtered. The filtercake is washed with water and air-dried to afford the title compound, 320 mg (54% yield), identified by NMR and mass spectral analyses.