2',4'-Dichloroacetophenone → 5-chloro-2-(2,4-dichlorophenyl)-1H-indole

HRID 966064

Reaction equation

HRID 966064 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]2

Participants

4

Reactant 2

HCID 166932',4'-DichloroacetophenoneHCID 70624(4-Chlorophenyl)hydrazine

Product 1

HCID 223142515-chloro-2-(2,4-dichlorophenyl)-1H-indoleYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe filtercake is washed with water
  4. customair-dried

Sources & evidence

ORD record
ord-e6b37ad3643848b9a4e6f97dd5da0c55
Source dataset
uspto-grants-2005_10
Patent number
US06951881B2

Linked notes

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