Benzocaine → Ethyl 4-amino-3-chlorobenzoate

HRID 1456138Notes

Reaction equation

HRID 1456138 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-8c22fd9f93f14631a20a627ca9fe3136
Source dataset
uspto-grants-1998_12
Patent number
US05843944

Reaction notes

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