Ammonia → 4-[4-(4-Chlorobenzoyl)benzyl]-3,5-dichloroaniline

HRID 1602881Notes

Reaction equation

HRID 1602881 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([N+:20]([O-])=O)=[CH:15][C:14]=3[Cl:23])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.N>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][C:16]([NH2:20])=[CH:15][C:14]=3[Cl:23])=[CH:10][CH:9]=2)=[O:7])=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 196083034-[4-(4-Chlorobenzoyl)benzyl]-3,5-dichloronitrobenzene

Product 1

HCID 196083004-[4-(4-Chlorobenzoyl)benzyl]-3,5-dichloroanilineYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 50 ml of ethyl acetate was dissolved 3.25 g of 4-[4-(4-chlorobenzoyl)benzyl]-3,5-dichloronitrobenzene, and 8.00 g of SnCl3.2H2O was added. The reaction mixture was refluxed for 1 hour, and then poured into ice-water. The mixture was alkalified with conc. ammonia solution, and the organic layer was collected by decantation. The aqueous layer was extracted twice with 50 ml of ethyl acetate, and the organic layers were combined, washed with water, dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2) to give the above-identified compound as pale brown amorphous powder (yield: 70%).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 1 hour
  3. customthe organic layer was collected by decantation
  4. extractionThe aqueous layer was extracted twice with 50 ml of ethyl acetate
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-11bcf332410b4858aeea2cfc2f63767d
Source dataset
uspto-grants-1999_11
Patent number
US05985875

Reaction notes

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