HCID 22624005, compound → HCID 22623908, compound

HRID 567050Notes

Reaction equation

HRID 567050 reaction equation
C([O:4][N:5]1[C:14](=[O:15])[C:13]2[C:16]([Cl:24])=[CH:17][C:18]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:11]3[C:12]=2[C:7](=[CH:8][CH:9]=[C:10]3[Cl:25])[C:6]1=[O:26])C=C>FC(F)(F)C(O)=O>[Cl:24][C:16]1[C:13]2[C:14](=[O:15])[N:5]([OH:4])[C:6](=[O:26])[C:7]3=[CH:8][CH:9]=[C:10]([Cl:25])[C:11]([C:12]=23)=[C:18]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:17]=1

Participants

3

Reactant 1

HCID 22624005HCID 22624005, compound

Product 1

HCID 22623908HCID 22623908, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-allyloxy-4,7-dichloro-6-(pyrrolidin-1-yl)benzo[de]isoquinoline-1,3-dione (0.5 g, 1.3 mmol, from Example J4) in trifluoroacetic acid (10 mL) was treated with boron tristrifluoroacetate (6 mL, 6.0 mmol, 1.0 M in trifluoroacetic acid). The reaction mixture was stirred at room temperature for 4 hours and evaporated in vacuo. The residue was chased with dichloro methane and redissolved in methanol which was also evaporated. The residue was partitioned between dichloromethane/water, separated, the organic layer dried, and evaporated in vacuo. The residue was triturated with petroleum ether, the solid removed by filtration, and dried in vacuo to give 0.2 g of the title compound, mp 243-245° C.

Workup

  1. customevaporated in vacuo
  2. dissolutionredissolved in methanol which
  3. customwas also evaporated
  4. customThe residue was partitioned between dichloromethane/water
  5. customseparated
  6. customthe organic layer dried
  7. customevaporated in vacuo
  8. customThe residue was triturated with petroleum ether
  9. customthe solid removed by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-74f45c9ffda24e07915597191d31047c
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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