N-tert-butyl-2-nitro-4-(trifluoromethyl)aniline → HCID 18509812, compound

HRID 1256623Notes

Reaction equation

HRID 1256623 reaction equation
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[N+:16]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([NH:5][C:6]1[C:7]([NH2:16])=[CH:8][C:9]([C:12]([F:14])([F:15])[F:13])=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 2736447N-tert-butyl-2-nitro-4-(trifluoromethyl)aniline

Product 1

HCID 18509812HCID 18509812, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.25 g of N-tert-butyl-2-nitro-4-trifluoromethylaniline, 20 ml of ethyl acetate and 5% palladium charcoal was stirred for 9 hours at room temperature under a hydrogen atmosphere of about 1 atm. The reaction mixture was filtrated through Celite (registered trademark). The filtrate was washed with water, dried over sodium sulfate, then, concentrated under reduced pressure to obtain a residue. The resultant residue was subjected to silica gel chromatography to obtain 4.82 g of N1-tert-butyl-4-trifluoromethylbenzene-1,2-diamine.

Workup

  1. filtrationThe reaction mixture was filtrated through Celite (registered trademark)
  2. washThe filtrate was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a residue

Sources & evidence

ORD record
ord-5075bff341504c0e81c816b14e578837
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

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