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

HRID 1651480Notes

Reaction equation

HRID 1651480 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([CH3:18])[C:12]1=[O:19].[N+:20]([O-])([OH:22])=[O:21]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]([N+:20]([O-:22])=[O:21])[C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[C:14]([CH3:17])=[C:13]([CH3:18])[C:12]1=[O:19]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 17802078N-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

26.3 g of N-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide are introduced in portions, at 5°, into 230 ml of 96% sulphuric acid. There is then added dropwise to this mixture, while stirring vigorously at the same temperature, 5 ml of 100% nitric acid. The whole is further stirred overnight at room temperature and then poured onto ice. The product which precipitates is filtered with suction, washed with water, dried and recrystallised from acetonitrile. 28 g of N-(2-fluoro-5-carboxy-4-nitrophenyl)-2,3-dimethylmaleic acid imide which has a melting point of 264°-265° is thus obtained.

Workup

  1. additionThere is then added dropwise to this mixture
  2. additionpoured onto ice
  3. customThe product which precipitates
  4. filtrationis filtered with suction
  5. washwashed with water
  6. customdried
  7. customrecrystallised from acetonitrile
  8. customis thus obtained

Sources & evidence

ORD record
ord-d8c70f73e1184262bfd31690282f997a
Source dataset
uspto-grants-1990_05
Patent number
US04929272

Reaction notes

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