Nitrogen → 2-(2-Dimethylaminoethoxy)-4-nitroanisole

HRID 1875397Notes

Reaction equation

HRID 1875397 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].Cl.Cl[CH2:15][CH2:16][N:17]([CH3:19])[CH3:18].[H-].[Na+].N#N>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[O:12][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 694712-Methoxy-5-nitrophenolHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 107764242-(2-Dimethylaminoethoxy)-4-nitroanisoleYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 2-methoxy-5-nitro-phenol (10 g), (2-chloro-ethyl)-dimethyl-amine hydrochloride (9.37 g) in dimethylformamide (150 mL) was added NaH (2.98 g) slowly under N2 and at room temperature. The mixture was then stirred at 140° C. heating with an oil bath for 5 hours. The reaction was concentrated to dryness, dissolved in 2 M HCl (200 mL) and washed with ethyl acetate (2×100 mL). The aqueous layer was basified with K2CO3, extracted with dichloromethane (3×200 mL) and ethyl acetate (2×100 mL), dried over Na2SO4, filtered, concentrated to give [2-(2-Methoxy-5-nitro-phenoxy)-ethyl]-dimethylamine (9.17 g, 65% yield). LCMS (m/z) M+H: 241.1.

Workup

  1. customat room temperature
  2. temperatureheating with an oil bath for 5 hours
  3. concentrationThe reaction was concentrated to dryness
  4. dissolutiondissolved in 2 M HCl (200 mL)
  5. washwashed with ethyl acetate (2×100 mL)
  6. extractionextracted with dichloromethane (3×200 mL) and ethyl acetate (2×100 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-eeb72cda0e5a4a9d987e49c30ac548e1
Source dataset
uspto-grants-2012_11
Patent number
US08309548B2

Reaction notes

Loading…