N-(2-fluoro-4-nitro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide → N-(2-fluoro-5-carboxy-4-aminophenyl)-2,3-dimethylmaleic acid imide

HRID 1381832Notes

Reaction equation

HRID 1381832 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[N:14]1[C:18](=[O:19])[C:17]([CH3:20])=[C:16]([CH3:21])[C:15]1=[O:22].[H][H]>[Ni].O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[N:14]1[C:15](=[O:22])[C:16]([CH3:21])=[C:17]([CH3:20])[C:18]1=[O:19]

Participants

5

Reactant 2

HCID 54493468N-(2-fluoro-4-nitro-5-carboxyphenyl)-2,3-dimethylmaleic acid imideHCID 178418361HCID 178418361, compound

Product 1

HCID 17802076N-(2-fluoro-5-carboxy-4-aminophenyl)-2,3-dimethylmaleic acid imideYield 92.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

67.8 g of N-(2-fluoro-5-carboxy-4-nitrophenyl)-2,3-dimethylmaleic acid imide are hydrogenated using hydrogen in the presence of 14 g of Raney nickel catalyst in 1000 ml of tetrahydrofuran at a temperature of 20°-25° under normal pressure. When the stoichiometric amount of hydrogen has been consumed, the catalyst is separated off and the solution is concentrated by evaporation. 56.7 g of N-(2-fluoro-5-carboxy-4-aminophenyl)-2,3-dimethylmaleic acid imide having a melting point of 270° are thus obtained.

Workup

  1. customat a temperature of 20°-25°
  2. customWhen the stoichiometric amount of hydrogen has been consumed
  3. customthe catalyst is separated off
  4. concentrationthe solution is concentrated by evaporation

Sources & evidence

ORD record
ord-f2e2eea0f93241a6a33c16d935641036
Source dataset
uspto-grants-1989_02
Patent number
US04804400

Reaction notes

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