Ethanol → 4-(Trifluoromethoxy)benzene-1,2-diamine

HRID 1428394Notes

Reaction equation

HRID 1428394 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.CCO.[Cl-].[NH4+]>[Zn].O>[F:13][C:12]([F:14])([F:15])[O:11][C:9]1[CH:10]=[C:4]([NH2:1])[C:5]([NH2:6])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 27757722-Nitro-4-(trifluoromethoxy)aniline

Product 1

HCID 27739594-(Trifluoromethoxy)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 2-nitro-4-(trifluoromethoxy)aniline (1.17 g) and EtOH (20 mL) were added ammonium chloride (565 mg) and water (5 mL), followed by further adding zinc powder (1.73 g) at 60° C., and heating and stirring at 60° C. for 1 hour. The reaction mixture was cooled to room temperature, filtered over Celite, and washed with EtOAc. This filtrate was washed with a saturated aqueous NaHCO3 solution and brine in this order, dried over MgSO4, and then concentrated under reduced pressure to obtain 4-(trifluoromethoxy)benzene-1,2-diamine.

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered over Celite
  4. washwashed with EtOAc
  5. washThis filtrate was washed with a saturated aqueous NaHCO3 solution and brine in this order
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6395519b5acf4c2cb750213db2fd074f
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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