3,4,5,6-Tetrahydrophthalic anhydride → N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1284616Notes

Reaction equation

HRID 1284616 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].[C:12]1(=O)[O:17][C:15](=[O:16])[C:14]2[CH2:18][CH2:19][CH2:20][CH2:21][C:13]1=2>C(O)(=O)C.O>[F:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[N:4]1[C:15](=[O:16])[C:14]2[CH2:18][CH2:19][CH2:20][CH2:21][C:13]=2[C:12]1=[O:17]

Participants

5

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 13560456N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimideYield 77.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2-Fluoro-5-nitroaniline (IV) (50 g) and 3,4,5,6-tetrahydrophthalic anhydride (49 g) were dissolved in acetic acid (200 ml), and the resultant solution was heated under reflux for 4 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was concentrated, and the precipitated crystals were collected by filtration to give 72 g of N-(2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide (VII). M.P., 154.9° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-de5c847609954841b93008abc8ac9692
Source dataset
uspto-grants-1986_01
Patent number
US04563535

Reaction notes

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