Hydrochloric Acid → 4-Amino-2-chlorobenzophenone

HRID 1288411Notes

Reaction equation

HRID 1288411 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° - 130° C. Crystallization from benzene-hexane gave faint yellow crystals of 4-amino-2-chlorobenzophenone having a melting point of 144° - 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° - 130° C
  9. customCrystallization from benzene-hexane

Sources & evidence

ORD record
ord-b2b8aed4cc284f52af5e1cca5d717b28
Source dataset
uspto-grants-1976_10
Patent number
US03988300

Reaction notes

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