Toluene → HCID 67993030, compound

HRID 879017Notes

Reaction equation

HRID 879017 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:8](CC)(CC)CC.[C:15]1(=[O:25])[O:20][C:18](=O)[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12>O>[C@@H:1]1([N:8]2[C:15](=[O:25])[C:16]3[C:17](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:18]2=[O:20])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6811Phthalic AnhydrideHCID 8471Triethylamine

Product 1

HCID 67993030HCID 67993030, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g of Cyclohex-3-enyl-1(R)-amine hydrochloride (Example 3 Step A2) and 40 ml of toluene was charged to a flask at RT and the mixture obtained was stirred. To the mixture obtained 1.9 ml of (C2H5)3N was added dropwise, the mixture obtained was stirred for 10 min followed by 1.12 g of phthalic anhydride and the mixture obtained was heated to reflux, with H2O removed under Dean-Stark conditions, until reaction completion (determined by HPLC). The mixture obtained was washed with 0.1 M HCl followed by 5% NaHCO3 and H2O, dried over Na2SO4 and concentrated to dryness. 1.20 g of 2-(cyclohex-3-en-1(R)-yl)-isoindole-1,3-dione in the form of a pale white crystalline solid was obtained.

Workup

  1. customthe mixture obtained
  2. additionwas added dropwise
  3. customthe mixture obtained
  4. stirringwas stirred for 10 min
  5. customthe mixture obtained
  6. temperaturewas heated
  7. customremoved under Dean-Stark conditions, until reaction completion (determined by HPLC)
  8. customThe mixture obtained
  9. washwas washed with 0.1 M HCl
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-92bfa40b983a4b55b073b7ae89f3ceda
Source dataset
uspto-grants-2015_03
Patent number
US08987498B2

Reaction notes

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