Benzocaine → Ethyl 4-amino-3-chlorobenzoate

HRID 1441031Notes

Reaction equation

HRID 1441031 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>C(#N)C>[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-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of ethyl 4-aminobenzoate (16 g.) in dry acetonitrile (200 ml.) at 60° was added N-chlorosuccinimide (13.35 g.) over 30 minutes. When the exothermic reaction had subsided the mixture was heated to reflux for 4 hours. After cooling the acetonitrile was removed under vacuum and the residue dissolved in dichloromethane. This was washed with 5% sodium hydroxide solution (2×100 ml.), brine and the organic layer dried over anhydrous magnesium sulphate. Evaporation yielded a solid that was purified by column chromatography on silica eluting with 10% ether/hexane.

Workup

  1. customWhen the exothermic reaction
  2. temperaturewas heated
  3. temperatureto reflux for 4 hours
  4. customwas removed under vacuum
  5. dissolutionthe residue dissolved in dichloromethane
  6. washThis was washed with 5% sodium hydroxide solution (2×100 ml.), brine
  7. dry with materialthe organic layer dried over anhydrous magnesium sulphate
  8. customEvaporation
  9. customyielded a solid
  10. customthat was purified by column chromatography on silica eluting with 10% ether/hexane

Sources & evidence

ORD record
ord-e841f91662f64ffba4504c0d8aa47e30
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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