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

HRID 402527Notes

Reaction equation

HRID 402527 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.CCCCCCC.C(OCC)(=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

7

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)-oneYield 54.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a solution of 9.17 g (51.8 mmol) of 6-fluoro-7-methyl-2H-isoquinolin-1-one in 80 ml of DMF were added 20.2 g (62.1 mmol) of cesium carbonate and then 8.92 g (56.9 mmol) of 4-methoxybenzylchloride. After stirring at room temperature for 90 minutes the reaction mixture was poured into 600 ml of water, stirred for 1 h, and then the precipitated product was isolated by suction. From the mother liquor additional product was isolated by chromatography with heptane/ethyl acetate (80:20). The combined products were recrystallized from ethyl acetate and 8.39 g of 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one were obtained.

Workup

  1. stirringstirred for 1 h
  2. customthe precipitated product was isolated by suction
  3. customThe combined products were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-fa3fa7b9c15b46288b27289d43ff887e
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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