Water → 4-Chloro-2-isopropoxyaniline

HRID 518879Notes

Reaction equation

HRID 518879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.O>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 23447873HCID 23447873, compound

Product 1

HCID 234479024-Chloro-2-isopropoxyanilineYield 102.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2.55 g of 4-chloro-1-nitro-2-(propan-2-yloxy)benzene in 40 ml of acetic acid is heated at 50° C., and then 7 ml of water and 2.64 g of iron powder are added. The mixture is stirred for 1 h at 50° C., and then cooled to ambient temperature and filtered on Celite. The Celite is rinsed three times with 20 ml of methanol, and the filtrate is concentrated under reduced pressure. The residue is taken up in 50 ml of 1N sodium hydroxide and 50 ml of dichloromethane. The aqueous phase is extracted twice with 50 ml of dichloromethane. The combined organic phases are dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure, so as to obtain 2.25 g of 4-chloro-2-(propan-2-yloxy)aniline in the form of a green oil.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered on Celite
  3. washThe Celite is rinsed three times with 20 ml of methanol
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. extractionThe aqueous phase is extracted twice with 50 ml of dichloromethane
  6. dry with materialThe combined organic phases are dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-27133c5ec38748e28961a708cf275639
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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