HCID 18694899, compound → HCID 15871216, compound

HRID 726140Notes

Reaction equation

HRID 726140 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[N+:15]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:6]=1[NH2:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18694899HCID 18694899, compound

Product 1

HCID 15871216HCID 15871216, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-t-butyl-5-trifluoromethylnitrobenzene (26.0 g, 105 mmol) in ethanol (95%, 100 mL) is treated with 10% Pd/C (2 g) and placed under a hydrogen atmosphere (40 psi) on a Parr apparatus for 1.5 h. The mixture is filtered, concentrated and purified by silica gel chromatography (7:1 hexane to ethyl acetate) to give 2-t-butyl-5-trifluoromethylaniline as an oil; yield: 20.2 g (89%).

Workup

  1. customfor 1.5 h
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (7:1 hexane to ethyl acetate)

Sources & evidence

ORD record
ord-7d4bf1e89b1442d989f0e1f204e0e649
Source dataset
uspto-grants-1998_01
Patent number
US05708001

Reaction notes

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