4,5-Dichloro-2-nitrophenol → 2-Amino-4,5-dichlorophenol

HRID 588767

Reaction equation

HRID 588767 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1>C(O)(=O)C.O.[Fe]>[NH2:10][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[CH:6][C:5]=1[OH:9]

Participants

5

Reactant 1

HCID 382484,5-Dichloro-2-nitrophenol

Product 1

HCID 30154152-Amino-4,5-dichlorophenolYield 78%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4,5-dichloro-2-nitrophenol (15 g, 72 mmol) in acetic acid (150 mL) and water (450 mL), iron powder (16 g, 285 mmol) was added in portions. The resulting mixture was stirred at 50° C. for 2 h. The mixture was allowed to cool to room temperature, filtered, and the cake was rinsed with ethyl acetate. The filtrate was extracted with ethyl acetate. The organic layer was washed with water, NaHCO3 (aq.) and brine, dried over Na2SO4 and concentrated in vacuo to afford the desired product (10 g, 78%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washthe cake was rinsed with ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washThe organic layer was washed with water, NaHCO3 (aq.) and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bff78745c1124b84b578a242800471d8
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Linked notes

Loading…