Water → N-[2-(dimethylamino)ethyl]benzene-1,2-diamine

HRID 252630Notes

Reaction equation

HRID 252630 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.O.[H][H]>[Pd].CO>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[C:7]([NH2:12])=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 430957N-(2-(dimethylamino)ethyl)-2-nitrobenzenamineHCID 178418361HCID 178418361, compound

Product 1

HCID 522698N-[2-(dimethylamino)ethyl]benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(2-(dimethylamino)ethyl)-2-nitrobenzenamine (2.0 g, 14 mmol) and 10% palladium on carbon, wet, 50% water (3.0 g) were combined under nitrogen. 30 mL MeOH was added via syringe, and the atmosphere was replaced with hydrogen from a balloon. The reaction was stirred rapidly for 20 h, at which point the reaction was flushed with nitrogen, and filtered through a pad of Celite®, and concentrated in vacuo to give N1-(2-(dimethylamino)ethyl)benzene-1,2-diamine as a red-brown solid. This material was used without further purification. MS m/z=180 [M+H]+. Calc'd for C10H17N3: 179.3.

Workup

  1. customwas flushed with nitrogen
  2. filtrationfiltered through a pad of Celite®
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d631805385e34b7d996d170eb0d38b1e
Source dataset
uspto-grants-2011_01
Patent number
US07868177B2

Reaction notes

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