2-Methoxyaniline → 2-methoxy-N-(2-methoxyethyl)aniline

HRID 565178Notes

Reaction equation

HRID 565178 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH3:10][O:11][CH2:12][CH2:13]Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:10][O:11][CH2:12][CH2:13][NH:9][C:4]1[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=1)[O:2][CH3:1]

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl ether

Product 1

HCID 15890502-methoxy-N-(2-methoxyethyl)anilineYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 24.6 g (200 mmol) o-anisidine M10, 20.8 g (220 mmol) chloroethyl methyl ether M11, 30.4 g (220 mmol) K2CO3 and 18.3 g (110 mmol) KI in 110 ml DMF was heated at 95° C. for 24 hours. DMF was evaporated, and the residue was digested with 100 ml CHCl3, filtered, and the precipitate washed with 2×50 ml CHCl3. The solvent was evaporated to give 41.2 g crude oil. This oil was purified by a plug packed with 184 g silica gel 100 with CHCl3/cyclohexane (1:1, v/v) as eluant, to afford 23.5 g pure product (yield: 65%).

Workup

  1. customDMF was evaporated
  2. filtrationfiltered
  3. washthe precipitate washed with 2×50 ml CHCl3
  4. customThe solvent was evaporated
  5. customto give 41.2 g crude oil
  6. customThis oil was purified by a plug

Sources & evidence

ORD record
ord-2f5d5daa013a4bc1b544cea3c2debd7f
Source dataset
uspto-grants-2001_01
Patent number
US06171866B2

Reaction notes

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