4-Methoxyphenol → Methyl 2-[3-(4-methoxyphenoxy)propyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616142Notes

Reaction equation

HRID 1616142 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=2)[C:6]1=[O:19].C(=O)([O-])[O-].[K+].[K+].[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1>CN(C=O)C>[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:2][CH2:3][CH2:4][N:5]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][C:9]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=3)[C:6]2=[O:19])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 67282659Methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67281827Methyl 2-[3-(4-methoxyphenoxy)propyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 2-(3-bromopropyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (80 mg, 0.25 mmol) in DMF (2.5 mL) was added potassium carbonate (68 mg, 0.50 mmol) and 4-methoxyphenol (61 mg, 0.50 mmol). The reaction mixture was heated to 40° C. and stirred overnight. The mixture was then cooled to rt, filtered and concentrated to afford methyl 2-[3-(4-methoxyphenoxy)propyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate. LC-MS: (FA) ES+ 368.

Workup

  1. temperatureThe mixture was then cooled to rt
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cbb0fabcc38f4a2e87f4cf4fa23abad1
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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