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

HRID 1256621Notes

Reaction equation

HRID 1256621 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-889cbbaf632545cd9f01a8b5b94ab524
Source dataset
uspto-grants-2013_06
Patent number
US08461181B2

Reaction notes

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