Ethyl Acetate → 1-(2-(2-Methoxy-4-nitrophenoxy)ethyl)pyrrolidine

HRID 532433

Reaction equation

HRID 532433 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:11]=[C:12]([OH:18])[C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)([O-:9])=[O:8].Cl.ClC[CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.[C:28](OCC)(=O)C>CN(C=O)C.O>[CH3:28][O:18][C:12]1[CH:11]=[C:10]([N+:7]([O-:9])=[O:8])[CH:15]=[CH:14][C:13]=1[O:16][CH2:17][CH2:22][N:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenolHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 179893551-(2-(2-Methoxy-4-nitrophenoxy)ethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (3.3 g) was added to a solution of 4-nitroguaiacol (1.0 g) and 1-(2-chloroethyl)pyrrolidine hydrochloride (1.0 g) in DMF (20.0 mL), and the mixture was heated at 100° C. overnight. The reaction mixture was then mixed with ethyl acetate and water, and the organic phase was washed twice with water, dried over sodium sulfate and concentrated. The product with the molecular weight of 266.3 (C13H18N2O4) was obtained in this way; MS (ESI): 267 (M+H+).

Workup

  1. washthe organic phase was washed twice with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe product with the molecular weight of 266.3 (C13H18N2O4) was obtained in this way

Sources & evidence

ORD record
ord-25ff1ee11c9f40fc841bf714f6d2c747
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Linked notes

Loading…