N-Isopropyl-2-Nitro-4-(Trifluoromethyl)Aniline → N~1~-(Propan-2-yl)-4-(trifluoromethyl)benzene-1,2-diamine

HRID 2390496Notes

Reaction equation

HRID 2390496 reaction equation
[CH:1]([NH:4][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)([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[CH:1]([NH:4][C:5]1[C:6]([NH2:15])=[CH:7][C:8]([C:11]([F:13])([F:14])[F:12])=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 2775213N-Isopropyl-2-Nitro-4-(Trifluoromethyl)Aniline

Product 1

HCID 735814N~1~-(Propan-2-yl)-4-(trifluoromethyl)benzene-1,2-diamineYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.46 g of N-isopropyl-2-nitro-4-trifluoromethylaniline, 30 ml of ethyl acetate and 5% palladium charcoal (catalytic amount) was stirred for 1.5 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 4.35 g of N1-isopropyl-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

Sources & evidence

ORD record
ord-178d82b7b84d4a6a8a09a02002d2017e
Source dataset
uspto-grants-2012_09
Patent number
US08273764B2

Reaction notes

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