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

HRID 1690549Notes

Reaction equation

HRID 1690549 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12](=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[CH3:10]>C(#N)C>[CH2:9]([O:11][C:12](=[O:21])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([NH2:20])=[C:18]([Cl:1])[CH:19]=1)[CH3:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 17859298(4-Amino-3-chloro-phenyl)-acetic acid ethyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

N-Chlorosuccinimide (391 mg, 2.93 mmol) was added to a solution of (4-amino-phenyl)-acetic acid ethyl ester (500 mg, 2.79 mmol; [5438-70-0]) in acetonitrile (10 ml) under an argon atmosphere. The reaction mixture was heated to 50° C. for 1 h. The solvent was removed under reduced pressure and the residue taken up in iPrOAc/brine 1/1. The layers were separated and the aqueous layer was extracted with iPrOAc. The combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, iPrOAc/heptane) to give the title compound (481 mg, 2.25 mmol; 81%) as brown oil. MS: m/e=214.1 [M+H+].

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with iPrOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, iPrOAc/heptane)

Sources & evidence

ORD record
ord-d58dd348a94a4787886ee5ef76da2077
Source dataset
uspto-grants-2012_04
Patent number
US08153663B2

Reaction notes

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