Ethyl chloroformate → N-(4-methoxyphenyl)isatoic anhydride

HRID 1980484Notes

Reaction equation

HRID 1980484 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.Cl[C:20](OCC)=[O:21]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:20](=[O:21])[O:14][C:12](=[O:13])[C:11]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]23)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 2029182-[(4-Methoxyphenyl)amino]benzoic acid

Product 1

HCID 13505629N-(4-methoxyphenyl)isatoic anhydride

Procedure

A suspension of 40 g of 2-(4-methoxyphenylamino)benzoic acid in 200 ml of ethyl chloroformate was heated at reflux for 24 hours. The reaction mixture was cooled in an ice-bath and the solid which separated was collected by filtration to give 31 g of N-(4-methoxyphenyl)isatoic anhydride after 6 hours of drying in a vacuum oven. An additional 9 g of product was obtained by concentration of the filtrate in vacuo.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture was cooled in an ice-bath
  4. customthe solid which separated
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-88d34012c6f74c0c911dc4331de9c6a5
Source dataset
uspto-grants-1985_04
Patent number
US04510139

Reaction notes

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