Ammonium Chloride → 4'-Amino-3'-(3-chlorophenoxy)acetophenone

HRID 1607670Notes

Reaction equation

HRID 1607670 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[O:5][C:6]1[CH:7]=[C:8]([C:15](=[O:17])[CH3:16])[CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:12][C:11]1[CH:10]=[CH:9][C:8]([C:15](=[O:17])[CH3:16])=[CH:7][C:6]=1[O:5][C:4]1[CH:18]=[CH:19][CH:20]=[C:2]([Cl:1])[CH:3]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 100856823'-(3-Chlorophenoxy)-4'-nitroacetophenone

Product 1

HCID 102646554'-Amino-3'-(3-chlorophenoxy)acetophenoneYield 106.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3'-(3-chlorophenoxy)-4'-nitroacetophenone (2.4 g), iron powder (2.4 g) and ammonium chloride (0.24 g) in ethanol (32 ml) and water (16 ml) was refluxed with stirring for 1 hour. The insoluble was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (30 ml), washed with water (20 ml), dried, and concentrated to give an oil of 4'-amino-3'-(3-chlorophenoxy)acetophenone (2.3 g).

Workup

  1. temperaturewas refluxed
  2. filtrationThe insoluble was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  5. washwashed with water (20 ml)
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-467118c75c144af6b713f0e27ab9bfb4
Source dataset
uspto-grants-1989_09
Patent number
US04866091

Reaction notes

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