3-Chloroaniline → HCID 11629788, compound

HRID 580883Notes

Reaction equation

HRID 580883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17](=[O:20])[CH2:18]Br.CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:18][C:17]([O:16][CH3:15])=[O:20])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 79323-ChloroanilineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 11629788HCID 11629788, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-chloroaniline and potassium carbonate (3 equiv.) in DMF is added methylbromoacetate (1.1 equiv.), and the reaction is stirred at 60° C. After complete reaction, the solution is poured into EtOAc and washed with water, sat. aq. NaHCO3 soln., and brine. The solution is dried (Na2SO4), filtered, and concentrated in vacuo. The resulting material is purified by silica gel chromatography to provide the titled compound.

Workup

  1. customAfter complete reaction
  2. washwashed with water, sat. aq. NaHCO3 soln
  3. dry with materialThe solution is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting material is purified by silica gel chromatography

Sources & evidence

ORD record
ord-a725d08ce0c04d57bccbf93f0443fb94
Source dataset
uspto-grants-1999_07
Patent number
US05919785

Reaction notes

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