Potassium Carbonate → 5-chloro-6,7-bis((4-methoxybenzyl)oxy)-3,4-dihydroisoquinolin-1(2H)-one

HRID 525847Notes

Reaction equation

HRID 525847 reaction equation
[Cl:1][C:2]1[C:11]([OH:12])=[C:10]([OH:13])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:14].[C:15](=[O:18])([O-])[O-].[K+].[K+].Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1>CN(C)C=O>[Cl:1][C:2]1[C:11]([O:12][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[C:10]([O:13][CH2:4][C:3]2[CH:8]=[CH:9][C:10]([O:18][CH3:15])=[CH:11][CH:2]=2)[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][C:7]2=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 717439535-Chloro-6,7-dihydroxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 867327155-chloro-6,7-bis((4-methoxybenzyl)oxy)-3,4-dihydroisoquinolin-1(2H)-oneYield 154.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the solution of 5-chloro-6,7-dihydroxy-3,4-dihydroisoquinolin-1(2H)-one (0.619 g, 2.9 mmol) in N,N-dimethylformamide (DMF) (10 mL) was added potassium carbonate (1.202 g, 8.70 mmol) followed by 1-(chloromethyl)-4-methoxybenzene (0.767 mL, 5.66 mmol). Stirred at room temperature for 4 hours. The mixture was extracted with ethyl acetate, washed with water, sodium chloride, and dried over magnesium sulfate. The crude mixture was chromotagraphed on silica ISCO column to give 5-chloro-6,7-bis((4-methoxybenzyl)oxy)-3,4-dihydroisoquinolin-1(2H)-one (1.017 g, 2.241 mmol, 77% yield). LCMS (M+H)+: 454.4

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with water, sodium chloride
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-c7d3e3288728495999dbaeeb9528ac54
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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