Water → N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 622295Notes

Reaction equation

HRID 622295 reaction equation
[Cl:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:5]([NH2:6])=[C:4]([F:12])[CH:3]=1.[C:13]1(=O)[O:18][C:16](=[O:17])[C:15]2[CH2:19][CH2:20][CH2:21][CH2:22][C:14]1=2.O>C(O)(=O)C>[Cl:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:5]([N:6]2[C:16](=[O:17])[C:15]3[CH2:19][CH2:20][CH2:21][CH2:22][C:14]=3[C:13]2=[O:18])=[C:4]([F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 137530614-Chloro-2-fluoro-5-nitroaniline

Product 1

HCID 15590179N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimideYield 61.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Chloro-2-fluoro-5-nitroaniline (19 g) and 3,4,5,6-tetrahydrophthalic anhydride (15.2 g) were dissolved in acetic acid (50 ml) and refluxed for 6 hours. After being allowed to cool, the resultant mixture was poured into water and extracted with toluene. The toluene layer was washed with water, an aqueous sodium hydrogen carbonate solution and water in order, dried and concentrated. The residue was crystallized from ethanol to give 20 g of N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide. M.P., 157°-157.5° C.

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureto cool
  3. extractionextracted with toluene
  4. washThe toluene layer was washed with water
  5. dry with materialan aqueous sodium hydrogen carbonate solution and water in order, dried
  6. concentrationconcentrated
  7. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-9d0b1a6c001f490d94a5e149e04d2d54
Source dataset
uspto-grants-1988_09
Patent number
US04770695

Reaction notes

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