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

HRID 1761325Notes

Reaction equation

HRID 1761325 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) are dissolved in acetic acid (50 ml) and refluxed for 6 hours. After being allowed to cool, the resultant mixture is poured into water and extracted with toluene. The toluene layer is washed with water, an aqueous sodium hydrogen carbonate solution and water in order, dried and concentrated. The residue is 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 is washed with water
  5. dry with materialan aqueous sodium hydrogen carbonate solution and water in order, dried
  6. concentrationconcentrated
  7. customThe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-6779cff59a2a4ad38b1e5cbbff0191d7
Source dataset
uspto-grants-1989_05
Patent number
US04826533

Reaction notes

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