2-Trifluoromethoxy-4-(phenyldiazenyl)phenol → 4-Amino-2-(trifluoromethoxy)phenol

HRID 900513Notes

Reaction equation

HRID 900513 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[C:8]([N:10]=NC2C=CC=CC=2)[CH:7]=[CH:6][C:5]=1[OH:18]>C(O)C.[Pd]>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([OH:18])=[C:4]([O:3][C:2]([F:1])([F:19])[F:20])[CH:9]=1

Participants

4

Reactant 1

HCID 1357029372-Trifluoromethoxy-4-(phenyldiazenyl)phenol

Product 1

HCID 113330044-Amino-2-(trifluoromethoxy)phenolYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

25 g (0.09 mol) of 2-trifluoromethoxy-4-(phenyldiazenyl)phenol from Example 7 and 1 g of Pd/C (10%) were initially charged in 350 ml of ethanol. The solution was degassed and aerated with hydrogen. The mixture was stirred at room temperature under a 1 bar hydrogen atmosphere for 72 hours. On completion of hydrogen uptake, the catalyst was filtered off and the filtrate concentrated on a rotary evaporator, in the course of which the product already crystallizes out. The resulting solid was filtered off with suction, washed with a little cold ethanol and dried under high vacuum for 4 hours. 8.5 g (50%) of the desired compound were obtained as a light brown powder.

Workup

  1. customThe solution was degassed
  2. filtrationOn completion of hydrogen uptake, the catalyst was filtered off
  3. concentrationthe filtrate concentrated on a rotary evaporator, in the course of which the product
  4. customalready crystallizes out
  5. filtrationThe resulting solid was filtered off with suction
  6. washwashed with a little cold ethanol
  7. customdried under high vacuum for 4 hours

Sources & evidence

ORD record
ord-186c7898d7e748ab84eac501a9606bef
Source dataset
uspto-grants-2008_04
Patent number
US07358397B2

Reaction notes

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