Phthalimide potassium salt → 1-((1,3-Dioxoisoindolin-2-yl)methyl)-6,7-dimethoxyisoquinolin-3-yl acetate

HRID 1620242Notes

Reaction equation

HRID 1620242 reaction equation
[C:1]([O:4][C:5]1[N:6]=[C:7]([CH2:19]Br)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=2)(=[O:3])[CH3:2].[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K]>CN(C=O)C.CCOCC.O>[C:1]([O:4][C:5]1[N:6]=[C:7]([CH2:19][N:25]2[C:21](=[O:31])[C:22]3[C:23](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:24]2=[O:26])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[C:10]([O:17][CH3:18])[CH:9]=2)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 681822701-(Bromomethyl)-6,7-dimethoxyisoquinolin-3-yl acetate2×

Product 1

HCID 681822081-((1,3-Dioxoisoindolin-2-yl)methyl)-6,7-dimethoxyisoquinolin-3-yl acetateYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(bromomethyl)-6,7-dimethoxyisoquinolin-3-yl acetate SIL 32162 (2.57 g, 7.56 mmol) in dry DMF (60 mL) in a 250 mL round-bottomed flask equipped with a magnetic stirrer was added potassium phthalimide (2.43 g, 13.12 mmol) and the mixture was stirred overnight at RT and then diluted with Et2O (150 mL) and H2O (40 mL). A solid appeared and was isolated by filtration. The aqueous phase was isolated and diluted with Et2O (100 mL) before vigorous stirring for 15 min, which gave a new amount of solid that was isolated by filtration (done 3 times). The solids were then combined, further washed with Et2O (100 mL) and dried overnight under vacuum in presence of P2O5, which gave 2.10 g of 1-((1,3-dioxoisoindolin-2-yl)methyl)-6,7-dimethoxyisoquinolin-3-yl acetate SIL 32166 as an off-white solid (68%).

Workup

  1. customwas isolated by filtration
  2. customThe aqueous phase was isolated
  3. stirringbefore vigorous stirring for 15 min
  4. customwhich gave a new amount of solid
  5. customthat was isolated by filtration (done 3 times)
  6. washfurther washed with Et2O (100 mL)
  7. dry with materialdried overnight under vacuum in presence of P2O5, which

Sources & evidence

ORD record
ord-2cee5f9083c648678b5c210c9001c2c0
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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