Methyl iodide → Methyl 1-cyclopropyl-5-methoxyisoquinoline-7-carboxylate

HRID 545210Notes

Reaction equation

HRID 545210 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][N:11]=[C:12]2[CH:15]2[CH2:17][CH2:16]2)=[C:7]([OH:18])[CH:6]=1)=[O:4].[C:19]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][N:11]=[C:12]2[CH:15]2[CH2:16][CH2:17]2)=[C:7]([O:18][CH3:19])[CH:6]=1)=[O:4]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57440909Methyl 1-cyclopropyl-5-hydroxyisoquinoline-7-carboxylate

Product 1

HCID 57440910Methyl 1-cyclopropyl-5-methoxyisoquinoline-7-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Cyclopropyl-5-hydroxy-isoquinoline-7-carboxylic acid methyl ester (5.00 g, 20.6 mmol) was dissolved in DMF (50 ml) and K2CO3 (5.69 g, 41.2 mmol) and MeI (1.54 ml, 24.7 mmol) was added thereto. After stirred at room temperature for 2 h, the reaction mixture was diluted with EtOAc and H2O. The aqueous layer was extracted with EtOAc and the organic layer was washed with brine, dried over MgSO4. The desiccant was removed through filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 6/4) to obtain the intended compound as a colorless solid.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customThe desiccant was removed through filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 6/4)

Sources & evidence

ORD record
ord-eaaa07596d8e4d10a58ae68c5aa3cc77
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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