N-(3-(dimethylamino)propyl)-N-methyl-3-nitro-5-(trifluoromethyl)pyridin-2-amine → N2-(3-(dimethylamino)propyl)-N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine

HRID 502707Notes

Reaction equation

HRID 502707 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][CH2:5][N:6]([CH3:20])[C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][C:10]([C:16]([F:19])([F:18])[F:17])=[CH:9][N:8]=1>CCO.[Ni]>[CH3:21][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]([CH3:20])[C:7]1[C:12]([NH2:13])=[CH:11][C:10]([C:16]([F:18])([F:19])[F:17])=[CH:9][N:8]=1

Participants

4

Reactant 1

HCID 68460853N-(3-(dimethylamino)propyl)-N-methyl-3-nitro-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 59427941N2-(3-(dimethylamino)propyl)-N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(3-(dimethylamino)propyl)-N-methyl-3-nitro-5-(trifluoromethyl)pyridin-2-amine (246 mg, 0.8 mmol) in EtOH was added Raney Nickel (700 mg, wet, washed). The reaction was allowed to stir for 2 h then filtered through a pad of Celite and concentrated under reduced pressure to afford N2-(3-(dimethylamino)propyl)-N2-methyl-5-(trifluoromethyl)pyridine-2,3-diamine. MS m/z=277 [M+H]+. Calc'd for C12H19F3N4: 276

Workup

  1. filtrationthen filtered through a pad of Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff75f76bfcdf45e1a32251c9dd0fa32b
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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