Acetic Acid → N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1709115Notes

Reaction equation

HRID 1709115 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:9]([F:13])=[CH:10][C:11]=1[Cl:12])[NH2:8])[CH:2]=[CH2:3].[CH2:14]1[CH:19]2[C:20]([O:22][C:23](=O)[CH:18]2[CH2:17][CH:16]=[CH:15]1)=[O:21].C(O)(=O)C>O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([N:8]2[C:20](=[O:21])[C:19]3[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=3[C:23]2=[O:22])[C:9]([F:13])=[CH:10][C:11]=1[Cl:12])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6810Tetrahydrophthalic anhydrideHCID 132729265-Allyloxy-4-chloro-2-fluoroaniline

Product 1

HCID 13151266N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.0 g of 19A, 6.8 g of THPA and 100 mL of glacial acetic acid was heated at reflux temperature for 4 hours. The resulting mixture was cooled to room temperature, poured into 450 mL of water and extracted with ether. The extract phase was washed with water, dried (Na2SO4), and filtered, and the solvent was evaporated from the filtrate. The residue was flash-chromatographed on silica gel, with a 15:85 v:v mixture of ethyl acetate and hexane as eluent, to give N-(3-(allyloxy)-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalimide (19B), as an orange oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 4 hours
  3. extractionextracted with ether
  4. washThe extract phase was washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated from the filtrate
  8. customThe residue was flash-chromatographed on silica gel, with a 15:85 v
  9. additionv mixture of ethyl acetate and hexane as eluent

Sources & evidence

ORD record
ord-c9ebfa4de63649a88eed276a98377b5f
Source dataset
uspto-grants-1990_08
Patent number
US04948418

Reaction notes

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