alpha,alpha,alpha-Trifluoro-3,5-dinitrotoluene → 5-(Trifluoromethyl)benzene-1,3-diamine

HRID 2352327Notes

Reaction equation

HRID 2352327 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([F:16])([F:15])[F:14])[CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:13]([F:14])([F:15])[F:16])[CH:7]=[C:8]([NH2:10])[CH:9]=1

Participants

5

Reactant 2

HCID 123060alpha,alpha,alpha-Trifluoro-3,5-dinitrotolueneHCID 178418361HCID 178418361, compound

Product 1

HCID 677815-(Trifluoromethyl)benzene-1,3-diamineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A 24.8 g sample of 3,5-dinitrobenzotrifluoride purchased from Aldrich Chemical Co. was slurried in 200 ml of ethanol and 5 g of 1% palladium on carbon added. This mixture was transferred to an autoclave, pressured to 400 psi with hydrogen, and heated at 75° C. with stirring for 1 hr. A 91% yield of pure 3,5-diaminobenzotrifluoride was recovered.

Sources & evidence

ORD record
ord-5a4f0008d0d44c0280f0433623697b67
Source dataset
uspto-grants-1989_10
Patent number
US04876329

Reaction notes

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