Hydrochloric Acid → 4-Amino-2-chlorobenzophenone

HRID 2398921Notes

Reaction equation

HRID 2398921 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Cl.[OH-].[NH4+].C(Cl)(Cl)Cl>C(O)C.O.[Fe]>[NH2:16][C:14]1[CH:13]=[CH:12][C:3]([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[C:2]([Cl:1])[CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14923Ammonium HydroxideHCID 884819(2-Chloro-4-nitrophenyl)(phenyl)methanone

Product 1

HCID 117364064-Amino-2-chlorobenzophenoneYield 69%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-chloro-4-nitrobenzophenone (27 grams, 0.103 mole) in hot ethanol (400 ml.) and water (200 ml.) was added iron (30 grams), followed by concentrated hydrochloric acid (25 ml.) dropwise and with stirring. After the addition, the reaction mixture was stirred at reflux during 1.5 hours, cooled, then made alkaline with ammonium hydroxide and chloroform extracted. After drying the chloroform layer (anhydrous MgSO4) and filtering, the solution was evaporated to an orange solid, melting point 120° C.-130° C. Crystallization from benzene-hexane gave faint yellow crystals of 4-amino-2-chlorobenzophenone having a melting point of 144° C.-145° C., and recovering 16.5 grams which amounts to a 69% yield.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred
  3. temperatureat reflux during 1.5 hours
  4. temperaturecooled
  5. extractionextracted
  6. dry with materialAfter drying the chloroform layer (anhydrous MgSO4)
  7. filtrationfiltering
  8. customthe solution was evaporated to an orange solid, melting point 120° C.-130° C
  9. customCrystallization from benzene-hexane

Sources & evidence

ORD record
ord-f05650be50b444b88b01f4746a969848
Source dataset
uspto-grants-1977_05
Patent number
US04026697

Reaction notes

Loading…