Ammonium Chloride → 3-amino-4-chlorobenzophenone

HRID 1902617Notes

Reaction equation

HRID 1902617 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])=[CH:6][C:5]=1[N+:18]([O-])=O>[Fe].CC1C=CC=CC=1>[NH2:18][C:5]1[CH:6]=[C:7]([C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:11])[CH:8]=[CH:9][C:4]=1[Cl:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 417434-Chloro-3-nitrobenzophenone

Product 1

HCID 107995483-amino-4-chlorobenzophenone

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 1140TolueneSolvent2×

Procedure

To a stirred and refluxing mixture of 11.2 parts of iron, 100 parts of ammonium chloride solution 0.8 N and 20 parts of methylbenzene are added 10.5 parts of (4-chloro-3-nitrophenyl)phenylmethanone and the whole is further stirred at reflux temperature of one hour. Methylbenzene (80 parts) is added and the whole is filtered over Hyflo. The organic layer is separated, dried, filtered and evaporated. The residue is washed with cyclohexane, yielding 8.4 parts of (3-amino-4-chlorophenyl)phenylmethanone; mp. 91.9° C.

Workup

  1. temperaturerefluxing
  2. stirringthe whole is further stirred
  3. temperatureat reflux temperature of one hour
  4. filtrationthe whole is filtered over Hyflo
  5. customThe organic layer is separated
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. washThe residue is washed with cyclohexane

Sources & evidence

ORD record
ord-5515db33c3734892b19a259f8981e947
Source dataset
uspto-grants-1982_12
Patent number
US04364942

Reaction notes

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