Chlorosuccinimide → (4-Amino-3-chloro-phenyl)-acetic acid ethyl ester

HRID 1879105Notes

Reaction equation

HRID 1879105 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[NH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][C:15]=1[Cl:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 17859298(4-Amino-3-chloro-phenyl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-chlorosuccinimide (1 eq, 7.45 g, 55.8 mmol) was added to a solution of ethyl 4-aminophenylacetate (10 g, 55.8 mmol) in chloroform (200 mls). The reaction mixture was stirred at room temperature, under argon, for 15 minutes. The reaction mixture was washed with water (250 mls) and the organic layer collected using a hydrophobic frit. This was evaporated to dryness to give a dark brown oil, 9.8 g.

Workup

  1. washThe reaction mixture was washed with water (250 mls)
  2. customthe organic layer collected
  3. customThis was evaporated to dryness
  4. customto give a dark brown oil, 9.8 g

Sources & evidence

ORD record
ord-61c7b41bf87b4e0e85ed50a818e217e2
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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