Hydrochloric Acid → 4-Amino-2,4'-dichlorobenzophenone

HRID 1361469Notes

Reaction equation

HRID 1361469 reaction equation
O.Cl.[Cl:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:14].O.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[O:14])=[C:4]([Cl:3])[CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8862964-Chlorophenyl 2-chloro-4-nitrophenyl ketoneHCID 86585896Sodium bicarbonate water

Product 1

HCID 30165104-Amino-2,4'-dichlorobenzophenoneYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

Iron powder (12 g), 42 mL of ethanol, 17 mL of distilled water, and 0.09 mL of 35% hydrochloric acid were mixed together, and the mixture was heated to reflux. Subsequently, (2-chloro-4-nitrophenyl)-(4′-chlorophenyl)methanone (8.9 g) dissolved in 12.8 mL of ethanol was added dropwise to the mixed solution, and the mixture was heated under reflux for one hr. This mixed solution was then cooled to room temperature, sodium bicarbonate water was then added thereto, and the mixture was filtered. The filtrate was concentrated under the reduced pressure, and ethyl acetate and brine were added to the residue, followed by separation. The ethyl acetate layer was washed with brine and was then concentrated under the reduced pressure to give 7.56 g of (4-amino-2-chlorophenyl)-(4′-chlorophenyl)methanone (yield 95%).

Workup

  1. temperaturethe mixture was heated to reflux
  2. additionwas added dropwise to the mixed solution
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for one hr
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure, and ethyl acetate and brine
  7. additionwere added to the residue
  8. customfollowed by separation
  9. washThe ethyl acetate layer was washed with brine
  10. concentrationwas then concentrated under the reduced pressure

Sources & evidence

ORD record
ord-05d617c07cff4d08b82b9222c8ff663f
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

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