3-Nitrophenol → 1-(2-Dimethylaminoethoxy)-3-nitrobenzene

HRID 450075Notes

Reaction equation

HRID 450075 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-].[K+].Cl.Cl[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18]>CS(C)=O>[CH3:18][N:17]([CH3:19])[CH2:16][CH2:15][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 14797Potassium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 218331171-(2-Dimethylaminoethoxy)-3-nitrobenzeneYield 40%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

3-Nitro phenol (1 g, 7.19 mmol) was added to a solution of potassium hydroxide (1.6 g, 28.76 mmol) in anhydrous DMSO (6 ml) at room temperature. After 30 min, (2-chloro-ethyl)-dimethyl-amine hydrochloride (1.03 g, 7.19 mmol) was added and the reaction mixture was heated at 80-90° C. for 12 hr. The reaction mixture was cooled to room temperature and diluted with ice water. The product was extracted with toluene and the organic layer was washed with 5% sodium hydroxide solution, then brine and dried. Evaporation under reduced pressure gave dimethyl-[2-(3-nitro-phenoxy)-ethyl]-amine (600 mg, 40%) as oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted with toluene
  3. washthe organic layer was washed with 5% sodium hydroxide solution
  4. dry with materialbrine and dried
  5. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-6de3891e9a0c43dda950b352bd62e5fa
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

Loading…