Tetrahydrophthalic anhydride → N-(3-(allyloxy)-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1709112Notes

Reaction equation

HRID 1709112 reaction equation
[CH2:1]1[CH:6]2[C:7]([O:9][C:10](=[O:11])[CH:5]2[CH2:4][CH:3]=[CH:2]1)=O.[CH2:12]([O:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[Cl:23])[NH2:19])[CH:13]=[CH2:14]>C(O)(=O)C>[CH2:12]([O:15][C:16]1[CH:17]=[C:18]([N:19]2[C:10](=[O:11])[C:5]3[CH2:4][CH2:3][CH2:2][CH2:1][C:6]=3[C:7]2=[O:9])[CH:20]=[CH:21][C:22]=1[Cl:23])[CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 6810Tetrahydrophthalic anhydrideHCID 544961134-Chloro-3-[(prop-2-en-1-yl)oxy]aniline

Product 1

HCID 12881900N-(3-(allyloxy)-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.4 g of THPA, 5.3 g of 3B and 60 mL of glacial acetic acid was refluxed for 1 hour, then poured into 300 mL of ice water. The resulting mixture was allowed to stand for 10 minutes, then filtered. The collected solid was washed with cold water, dried under reduced pressure and recrystallized from ethyl acetate/hexane, to give N-(3-(allyloxy)-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide (3C), as yellow crystals, m.p.: 118.5°-120° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationfiltered
  3. washThe collected solid was washed with cold water
  4. customdried under reduced pressure
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b9b8daf5be714887a0ede8864455c74b
Source dataset
uspto-grants-1990_08
Patent number
US04948418

Reaction notes

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