Benzocaine → Ethyl 4-amino-3-chlorobenzoate

HRID 440023Notes

Reaction equation

HRID 440023 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 and dried Na2SO4)
  3. washthe filter cake washed with dichloromethane
  4. concentrationThe filtrate is concentrated
  5. additionhexane added
  6. temperatureChilling

Sources & evidence

ORD record
ord-683954de824841cea62b315199d3e13c
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Reaction notes

Loading…