Benzocaine → Ethyl 4-amino-3-chlorobenzoate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureis refluxed overnight
- washThe mixture is washed with saturated NaHCO3 solution
- dry with materialdried (Na2SO4)
- washthe filter cake washed with dichloromethane
- concentrationThe filtrate is concentrated
- additionhexane added
- temperatureChilling
Sources & evidence
- ORD record
- ord-ad9d485deb4a410790b440b0d8fd2a4a
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05733905
Reaction notes
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