3-Chloroaniline → HCID 11629788, compound

HRID 2199787Notes

Reaction equation

HRID 2199787 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[Cl:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[C:8]([Cl:7])[CH:9]=1

Participants

6

Reactant 3

HCID 79323-ChloroanilineHCID 60984Methyl bromoacetateHCID 81531Diisopropylethylamine

Product 1

HCID 11629788HCID 11629788, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Methyl bromoacetate (8.3 g, 54.3 mmol), 3-chloroaniline (8.31 g, 65.1 mmol) and diisopropylethylamine (7.01 g, 54.3 mmol) were dissolved in N,N-dimethylformamide (20 mL) to give a light yellow solution and the reaction mixture heated at 60° C. overnight. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give (3-chloro-phenylamino)-acetic acid methyl ester as a solid which was washed with hexanes, filtered and dried (10.2 g, 96%).

Workup

  1. customto give a light yellow solution
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ccc3d19480d44790b2ab7c35c73afeff
Source dataset
uspto-grants-2016_06
Patent number
US09359345B2

Reaction notes

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