Hydrochloric Acid → 2-Amino-5-chlorobenzophenone

HRID 971615Notes

Reaction equation

HRID 971615 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.B(Cl)(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[OH-:18].[Na+].[C:20](#N)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCC(Cl)(Cl)Cl.C(Cl)Cl.C(O)C>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][C:4]=1[C:20]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 7505Benzonitrile2×HCID 78124-ChloroanilineHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 128702-Amino-5-chlorobenzophenone

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×HCID 124181,1,1,2-TetrachloroethaneSolvent2×

Procedure

To a solution of p-chloroaniline (640 mg) in tetrachloroethane (5 ml), a solution of boron trichloride (640 mg) in tetrachloroethane (2.5 ml), benzonitrile (1 ml) and aluminum chloride (734 mg) are added under ice cooling, and the resultant mixture is refluxed for 6 hours. After cooling, the reaction mixture is mixed with 2 N hydrochloric acid (10 ml), heated at 70° to 80° C. for 20 minutes, and shaken with methylene chloride. The methylene chloride layer is evaporated to give a residue, to which 95% ethanol (5 ml) and 2 N sodium hydroxide (10 ml) are added. The mixture is refluxed for 1 hour to hydrolyze benzonitrile and shaken with methylene chloride. The methylene chloride layer is evaporated, and the residue is dissolved in benzene and chromatographed on a column of alumina, which is eluted with benzene. The benzene eluate affords 2-amino-5-chlorobenzophenone (486 mg), which is recrystallized from ether to give crystals melting at 99° C.

Workup

  1. temperatureAfter cooling
  2. temperatureheated at 70° to 80° C. for 20 minutes
  3. customThe methylene chloride layer is evaporated
  4. customto give a residue
  5. temperatureThe mixture is refluxed for 1 hour
  6. customThe methylene chloride layer is evaporated
  7. dissolutionthe residue is dissolved in benzene
  8. customchromatographed on a column of alumina, which
  9. washis eluted with benzene

Sources & evidence

ORD record
ord-d6938ca8244f493c8bc374e0265190a8
Source dataset
uspto-grants-1979_07
Patent number
US04160784

Reaction notes

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