1-(4-Chloro-3-nitrophenoxy)-2-propanone → 1-(3-Amino-4-chlorophenoxy)-2-propanone

HRID 637688Notes

Reaction equation

HRID 637688 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:13]([O-])=O>[Ni].O1CCOCC1>[NH2:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[Cl:1])[O:6][CH2:7][C:8](=[O:10])[CH3:9]

Participants

4

Reactant 1

HCID 202556531-(4-Chloro-3-nitrophenoxy)-2-propanone

Product 1

HCID 202556581-(3-Amino-4-chlorophenoxy)-2-propanone

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 23.8 g (0.104 mole) of 1-(4-chloro-3-nitrophenoxy)-2-propanone, 2 g of Raney nickel and 240 ml of dioxane is hydrogenated at normal pressure and room temperature. After 20 hours (hydrogen absorption: 103%), the whole is filtered with suction over Celite, then washed with dioxane and concentrated by evaporation in vacuo. Purification of the crude product by chromatographed with petroleum ether/ether over silica gel and subsequent recrystallisation from ether/petroleum ether yields 1-(3-amino-4-chlorophenoxy)-2-propanone having a melting point of 49°-51°.

Workup

  1. customis hydrogenated at normal pressure and room temperature
  2. customAfter 20 hours (hydrogen absorption: 103%)
  3. filtrationthe whole is filtered with suction over Celite
  4. washwashed with dioxane
  5. concentrationconcentrated by evaporation in vacuo
  6. customPurification of the crude product
  7. customby chromatographed with petroleum ether/ether over silica gel and subsequent recrystallisation from ether/petroleum ether

Sources & evidence

ORD record
ord-cb0315b64b9c43968813b6197e49a506
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

Loading…