Water → 6-fluoro-2-(4-methoxybenzyl)-7-methylisoquinolin-1(2H)-one

HRID 2370269Notes

Reaction equation

HRID 2370269 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[N:7]([CH2:26][C:25]1[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 592260506-Fluoro-7-methylisoquinolin-1(2H)-one

Product 1

HCID 592260436-fluoro-2-(4-methoxybenzyl)-7-methylisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9.17 g of 6-fluoro-7-methyl-2H-isoquinolin-1-one (12) in 80 ml DMF were added 20.2 g caesium carbonate and then 8.92 g 4-methoxybenzyl-chloride. After stirring at room temperature for 90 minutes the reaction mixture was poured into 600 ml water, stirred for 1 h, and then the precipitated product was filtrated by suction. From the mother liquor additional producted was isolated by chromatography with heptane/ethyl acetate (80:20). The combined products were recrystallized from ethyl acetate and 8.39 g 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one (13) were received. Rt=1.83 min (Method B). Detected mass: 298.1 (M+H+).

Workup

  1. stirringstirred for 1 h
  2. filtrationthe precipitated product was filtrated by suction
  3. customFrom the mother liquor additional producted was isolated by chromatography with heptane/ethyl acetate (80:20)
  4. customThe combined products were recrystallized from ethyl acetate and 8.39 g 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one (13)

Sources & evidence

ORD record
ord-ee34f233c8d3495e907cc46f547716e2
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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