Dimethylmaleic anhydride → N-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide

HRID 1651479Notes

Reaction equation

HRID 1651479 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].[CH3:12][C:13]1=[C:14]([CH3:20])[C:15]([O:17][C:18]1=O)=[O:16]>C(O)(=O)C>[F:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[N:1]1[C:15](=[O:16])[C:14]([CH3:20])=[C:13]([CH3:12])[C:18]1=[O:17]

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 753963-Amino-4-fluorobenzoic acid

Product 1

HCID 17802078N-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleic acid imideYield 89.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 46.5 g of 3-amino-4-fluorobenzoic acid and 37.8 g of dimethylmaleic anhydride in 200 ml of glacial acetic acid is stirred for 12 hours at an oil bath temperature of 130°-40°. After cooling, the mixture is poured onto ice-water, and the resulting precipitate is filtered with suction, washed with water and dried. Recrystallisation from ethanol/water yields 70.3 g of N-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide which melts at 238°-240°.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured onto ice-water
  3. filtrationthe resulting precipitate is filtered with suction
  4. washwashed with water
  5. customdried
  6. customRecrystallisation from ethanol/water

Sources & evidence

ORD record
ord-1b3c8aa58cdb4682bac0304ea02c373f
Source dataset
uspto-grants-1990_05
Patent number
US04929272

Reaction notes

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