HCID 68461880, compound → HCID 59427865, compound

HRID 502738Notes

Reaction equation

HRID 502738 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[CH3:9])=[C:4]([N+:16]([O-])=O)[CH:3]=1>CCO.O.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([N:8]([CH2:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 68461880HCID 68461880, compound

Product 1

HCID 59427865HCID 59427865, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 4-chloro-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine (4.0 g, 15 mmol) in EtOH (80 ml) and water (10 ml) was added Raney-Ni (10 g). The mixture was stirred for 5 hours at RT, filtered through a pad of Celite and concentrated to yield 4-chloro-N1-(3-(dimethylamino)propyl)-N1-methylbenzene-1,2-diamine as a deep red oil. MS m/z=242 [M+H+. Calc'd for C12H20ClN3: 241.77.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f2e968d6a85542ee98412410b670d2dc
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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