Water → HCID 28570573, compound

HRID 1592024Notes

Reaction equation

HRID 1592024 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].O>CN(C=O)C>[CH3:23][O:22][C:20](=[O:21])[CH2:19][NH:5][C:4]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 176522,4-DimethoxyanilineHCID 60984Methyl bromoacetate

Product 1

HCID 28570573HCID 28570573, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 1.53 g (10 mmol) of 2,4-dimethoxyaniline and 2.76 g (20 mmol) of potassium carbonate in 10 mL of DMF are added 1.53 g (10 mmol) of methyl bromoacetate. The mixture is stirred at 60° C. for 3 h, then allowed to cool to RT. The mixture is poured into water and extracted with EtOAc. The organic phase is washed with water, brine and dried over anhydrous Na2SO4. The solvent is removed under reduced pressure and the residue is chromatographed using CH2Cl2 as the eluant to give (2,4-dimethoxyphenylamino)-acetic acid methyl ester as an oil: 1H-NMR (CDCl3) δ 6.46 (d, J=2.20, 1H), 6.41-6.38 (m, 2H), 3.91 (s, 2H), 3.84 (s, 3H), 3.77 (s, 3H), 3.75 (s, 3H).

Workup

  1. temperatureto cool to RT
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is chromatographed

Sources & evidence

ORD record
ord-7f9aaa9aa63341e599f078ec9e53927e
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

Loading…