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 1925279Notes

Reaction equation

HRID 1925279 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 (Step a, 1.42 g, 4.65 mmol) in MeOH (47 mL) was added Pd/C (10%, 493 mg, 0.465 mmol). The mixture was stirred overnight under an atmosphere of H2. The mixture was filtered through a pad of Celite and concentrated to afford the title compound as a brown oil. M+H −276. Calc'd for C13H20F3N3−275.32.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-fe20796a1a604a33abfe8d4ec12723b3
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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