Hydrochloric Acid → Ethyl 3-(3-chloroanilino)propanoate

HRID 2427781Notes

Reaction equation

HRID 2427781 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][CH2:11][CH2:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 79323-ChloroanilineHCID 8821Ethyl Acrylate

Product 1

HCID 12646054Ethyl 3-(3-chloroanilino)propanoateYield 51.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Chloroaniline (3.8 g, 0.03 moles) was dissolved in ethanol (5 ml) and ethyl acrylate (3.3 g, 0.033 moles) was added in ethanol (5 ml). Concentrated hydrochloric acid (1 ml) was added and the reaction mixture was heated at reflux for 48 hours. Evaporated to a low bulk and dissolved the residue in dichloromethane and water. Basified to pH 9 with aqueous ammonia and separated. Evaporated off the dichloromethane under reduced pressure to give the crude product as a yellow oil (5.4 g) Purified using a silica column eluted with isohexane:ethyl acetate 9:1 to give the required product (3.5 g, 51%) as a colourless oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 48 hours
  3. customEvaporated to a low bulk
  4. dissolutiondissolved the residue in dichloromethane
  5. customseparated
  6. customEvaporated off the dichloromethane under reduced pressure
  7. customto give the crude product as a yellow oil (5.4 g)
  8. customPurified
  9. washeluted with isohexane:ethyl acetate 9:1

Sources & evidence

ORD record
ord-50491fc28305404d9f764129a3c66f8f
Source dataset
uspto-grants-2011_06
Patent number
US07968711B2

Reaction notes

Loading…