N-(3-(dimethylamino)propyl)-N-methyl-2-nitro-4-(trifluoromethyl)benzenamine → N~1~-[3-(dimethylamino)propyl]-N~1~-methyl-4-(trifluoromethyl)benzene-1,2-diamine

HRID 883038Notes

Reaction equation

HRID 883038 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][CH2:5][N:6]([CH3:20])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[N+:17]([O-])=O>CO.[Pd]>[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]([CH3:20])[C:7]1[C:8]([NH2:17])=[CH:9][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 16109008N-(3-(dimethylamino)propyl)-N-methyl-2-nitro-4-(trifluoromethyl)benzenamine

Product 1

HCID 16109009N~1~-[3-(dimethylamino)propyl]-N~1~-methyl-4-(trifluoromethyl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To N-(3-(dimethylamino)propyl)-N-methyl-2-nitro-4-(trifluoromethyl)benzenamine (1.46 g, 5.05 mmol) in dry MeOH (50 mL) was added Pd/C (10%, 535 mg). H2 gas was bubbled through the solution at room temperature overnight with vigorous stirring. The reaction mixture was filtered through celite to provide, after concentration, the title compound as an orange solid. MS m/z (M+H)+=276; Calc'd for C13H20F3N3: 275.32.

Workup

  1. customH2 gas was bubbled through the solution at room temperature overnight with vigorous stirring
  2. filtrationThe reaction mixture was filtered through celite
  3. customto provide
  4. concentrationafter concentration

Sources & evidence

ORD record
ord-fa23ca46d47649abae51ec5d75fb54b4
Source dataset
uspto-grants-2012_08
Patent number
US08236823B2

Reaction notes

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