Dimethylmaleic anhydride → HCID 17802077, compound

HRID 1651491Notes

Reaction equation

HRID 1651491 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([OH:10])=[CH:5][C:3]=1[NH2:4].[CH3:11][C:12]1=[C:13]([CH3:19])[C:14]([O:16][C:17]1=O)=[O:15]>C(O)(=O)CC>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([OH:10])=[CH:5][C:3]=1[N:4]1[C:14](=[O:15])[C:13]([CH3:19])=[C:12]([CH3:11])[C:17]1=[O:16]

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 1586545-Amino-2-chloro-4-fluorophenol

Product 1

HCID 17802077HCID 17802077, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

A mixture of 16.1 g of 2-fluoro-4-chloro-5-hydroxyaniline and 12.6 g of dimethylmaleic acid anhydride in 100 ml of propionic acid are heated to 150° and stirred for 12 hours at that temperature. The reaction mixture is then allowed to cool and concentrated. The residue is cristallized from methanol and yields 27.3 g of N-(2-fluoro-4-chloro-5-hydroxyphenyl)-2,3-dimethylmaleic acid imide melting at 170°-171°.

Workup

  1. temperatureare heated to 150°
  2. temperatureto cool
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-40d30e880f8c404f8514a6f994b674f9
Source dataset
uspto-grants-1990_05
Patent number
US04929272

Reaction notes

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