4-(2-(Dimethylamino)ethoxy)-2-nitroaniline → 4-(2-(Dimethylamino)ethoxy)benzene-1,2-diamine

HRID 415062Notes

Reaction equation

HRID 415062 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1.[H][H]>CO.[Pd]>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:10])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 593493934-(2-(Dimethylamino)ethoxy)-2-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 221677014-(2-(Dimethylamino)ethoxy)benzene-1,2-diamineYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a Parr hydrogenation bottle was added 3.5 g of 4-(2-(dimethylamino)ethoxy)-2-nitroaniline, 10% palladium in carbon (50% w/w water, 1.0 g) and methanol (100 mL). The atmosphere of the vessel was replaced by hydrogen gas. The reaction was carried out on the Parr shaker at 40 psi at room temperature for 1 hour. The reaction mixture was filtered through a plug of Celite. 2.0 g of sodium bicarbonate was subsequently added to the filtrate, which was stirred for 10 minutes. The filtrate was concentrated reduced pressure and the resulting residue was triturated with diethylether to give 4-(2-(dimethylamino)ethoxy)benzene-1,2-diamine (2.2 g, 73%). 1H-NMR (400 MHz, MeOH-d4): δ 6.67 (d, 1H), 6.44 (d, 1H), 6.27 (dd, 1H), 4.18 (t, 2H), 3.50 (t, 3H), 2.92 (s, 6H). MS (EI): 196 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through a plug of Celite
  2. addition2.0 g of sodium bicarbonate was subsequently added to the filtrate, which
  3. concentrationThe filtrate was concentrated reduced pressure
  4. customthe resulting residue was triturated with diethylether

Sources & evidence

ORD record
ord-853725cb0d8d4cbc96c6497201938076
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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