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

HRID 222425Notes

Reaction equation

HRID 222425 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)[CH3:2].[Cl:14]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([NH2:12])=[C:10]([Cl:14])[CH:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 17859298(4-Amino-3-chloro-phenyl)-acetic acid ethyl esterYield 42.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ethyl-4-aminophenylacetate (20 g, 112 mmol) was dissolved in chloroform (300 ml) and treated with N-chlorosuccinimide (14.92 g, 112 mmol) and stirred for 15 minutes at room temperature under argon. Reaction mixture was washed with water, brine and dried over magnesium sulphate. Evaporated to a brown oil which was purified by chromatography on silica gel eluting with ethyl acetate (0-45%) in hexane to give the title compound as a orange oil (10.12 g, 47.4 mmol). LC/MS: Rt=2.59, [MH]+ 214.

Workup

  1. customReaction mixture
  2. washwas washed with water, brine
  3. dry with materialdried over magnesium sulphate
  4. customEvaporated to a brown oil which
  5. customwas purified by chromatography on silica gel eluting with ethyl acetate (0-45%) in hexane

Sources & evidence

ORD record
ord-ead2d4b4bcc54d6d9465d87ca620ebe1
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

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