Acetone → 1,2-Dihydro-4-[4-(dimethylaminomethyl)phenyl]-5-hydroxy-1-oxoisoquinoline methanesulfonate

HRID 31109Notes

Reaction equation

HRID 31109 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[OH:21])[C:14](=[O:22])[NH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH3:3].[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].CC(C)=O>CO>[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[OH:21])[C:14](=[O:22])[NH:13][CH:12]=2)=[CH:9][CH:10]=1)[CH3:1]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6395Methanesulfonic AcidHCID 98390734-(4-((dimethylamino)methyl)phenyl)-5-hydroxyisoquinolin-1(2H)-one

Product 1

HCID 877322561,2-Dihydro-4-[4-(dimethylaminomethyl)phenyl]-5-hydroxy-1-oxoisoquinoline methanesulfonateYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of the compound of Example 1 (414 mg, 1.41 mmol) in methanol (15 mL) was added methanesulfonic acid (101 μL, 1.55 mmol), and the mixture was stirred for 30 minutes at room temperature. Acetone was added to the residue obtained by concentrating the reaction mixture under reduced pressure. The precipitated crystals were collected by filtration, washed with acetone, and then dried, thereby affording 492 mg of the title compound as light brown powder. Yield 88%.

Workup

  1. customobtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with acetone
  5. customdried

Sources & evidence

ORD record
ord-08be601c915f47659797027752908655
Source dataset
uspto-grants-2008_09
Patent number
US07425563B2

Reaction notes

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