4-Methoxyphenol → Methyl 2-[2-(4-methoxyphenoxy)ethyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616144Notes

Reaction equation

HRID 1616144 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].Br[CH2:17][CH2:18][N:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][C:23]([C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:25]=2)[C:20]1=[O:33]>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:17][CH2:18][N:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][C:23]([C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:25]=3)[C:20]2=[O:33])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 23665647Potassium tert-butoxideHCID 67281903Methyl 2-(2-bromoethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67283710Methyl 2-[2-(4-methoxyphenoxy)ethyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methoxyphenol (74 mg, 0.59 mmol) in THF (2.5 mL) was added potassium tert-butoxide (52 mg, 0.46 mmol). The reaction mixture was stirred at rt for 3 h, then methyl 2-(2-bromoethyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (80 mg, 0.26 mmol) in DMF (2.5 mL) was added and the resulting mixture was stirred at rt overnight. The mixture was then concentrated to afford methyl 2-[2-(4-methoxyphenoxy)ethyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate. LC-MS: (FA) ES+354.

Workup

  1. stirringthe resulting mixture was stirred at rt overnight
  2. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-6884bc943294445b84e28895e749ab17
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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