1,3-Dimethylimidazolium Iodide → 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile

HRID 1833258Notes

Reaction equation

HRID 1833258 reaction equation
[H-].[Na+].Br[C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7]([C:18]#[N:19])=[CH:6][N:5]=1.[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=[O:27])[CH3:21].[I-].C[N+]1C=CN(C)C=1>CN(C=O)C.C(Cl)Cl.O>[CH2:20]([O:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[C:26]([C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7]([C:18]#[N:19])=[CH:6][N:5]=1)=[O:27])[CH3:21]

Participants

8

Reactant 4

HCID 203341,3-Dimethylimidazolium IodideHCID 24758Sodium hydrideHCID 899083-EthoxybenzaldehydeHCID 220483501-Bromo-6,7-dimethoxyisoquinoline-4-carbonitrile

Product 1

HCID 220484311-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrileYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium hydride (0.21 g, 5.1 mmol) was added to a stirred mixture of 1-Bromo-6,7-dimethoxy-isoquinoline-4-carbonitrile (1.0 g, 3.4 mmol), 3-Ethoxy-benzaldehyde (0.72 mL, 5.1 mmol), 1,3-dimethylimidazolium iodide (0.32 g, 1.36 mmol) in DMF (40 mL). The reaction mixture became dark color. After 30 min, water was added to the above mixture, and extracted with chloroform. The extract was washed with water, dried over sodium sulfate, filtered and concentrated in vacuo to afford a solid. Flash chromatography (Merck Silica gel 60, 70–230 mesh, methylenechloride) afforded 1-(3-Ethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile (1.22 g, 98%) as a white solid. LC-MS m/e calcd for C21H18N2O4 (MH+) 363, found 363.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a solid

Sources & evidence

ORD record
ord-8834345f393b4f86a3dca429656687c4
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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