4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → 1-Hydroxy-6-(trifluoromethyl)benzotriazole

HRID 10755

Reaction equation

HRID 10755 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=O.O.[NH2:16][NH2:17]>C(O)C>[OH:14][N:12]1[C:3]2[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=2[N:17]=[N:16]1

Participants

4

Reactant 2

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 6881941-Hydroxy-6-(trifluoromethyl)benzotriazoleYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared according to the procedure described by K. Takeda [J. Org. Chem., 50, 273, (1985)]. A mixture of 4-chloro-3-nitro-α,α,α-trifluorotoluene (50.0 g, 0.22 moles) and hydrazine hydrate (33.0, 0.33 moles) in absolute ethanol (75 ml) is refluxed for 24 h. After removal of the solvent under reduced pressure, the residue is dissolved in 10% aqueous sodium carbonate solution. The solution is washed with ether to remove the starting material and acidified with concentrated HCl to precipitate the product, which is washed with water and dried to obtain 40.0 g of the title compound. This product is recrystallized from ether.

Workup

  1. customThe title compound is prepared
  2. temperatureis refluxed for 24 h
  3. customAfter removal of the solvent under reduced pressure
  4. dissolutionthe residue is dissolved in 10% aqueous sodium carbonate solution
  5. washThe solution is washed with ether
  6. customto remove the starting material
  7. customto precipitate the product, which
  8. washis washed with water
  9. customdried

Sources & evidence

ORD record
ord-868789ba44d24a379570d31b85128dc2
Source dataset
uspto-grants-2006_08
Patent number
US07094872B2

Linked notes

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