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

HRID 1638898Notes

Reaction equation

HRID 1638898 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-b41697cc08d94b38bbe5d189d9d3170e
Source dataset
uspto-grants-1989_11
Patent number
US04881970

Reaction notes

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