Benzocaine → Ethyl 4-amino-3-chlorobenzoate

HRID 1420053Notes

Reaction equation

HRID 1420053 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[Cl:13]N1C(=O)CCC1=O>ClCCl>[Cl:13][C:12]1[CH:11]=[C:5]([CH:4]=[CH:3][C:2]=1[NH2:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 31398Chlorosuccinimide

Product 1

HCID 1515285Ethyl 4-amino-3-chlorobenzoateYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8.26 g of ethyl 4-aminobenzoate, 8.26 g of N-chlorosuccinimide in 50 ml of dichloromethane is refluxed overnight. The mixture is washed with saturated NaHCO3 solution and dried (Na2SO4). The solution is passed through a thin pad of hydrous magnesium silicate and the filter cake washed with dichloromethane. The filtrate is concentrated and hexane added. Chilling gives 7.38 g of ethyl 3-chloro-4-aminobenzoate, m.p. 82°-83° C.

Workup

  1. temperatureis refluxed overnight
  2. washThe mixture is washed with saturated NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. washthe filter cake washed with dichloromethane
  5. concentrationThe filtrate is concentrated
  6. additionhexane added
  7. temperatureChilling

Sources & evidence

ORD record
ord-e30a786d35ad4876956d12a9e0d00a51
Source dataset
uspto-grants-1999_03
Patent number
US05889001

Reaction notes

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