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

HRID 1833262Notes

Reaction equation

HRID 1833262 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.[OH:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=[O:28].[I-].C[N+]1C=CN(C)C=1>CN(C=O)C.C(Cl)Cl.CCOC(C)=O.O>[OH:20][CH2:21][CH2:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]([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:28]

Participants

9

Reactant 4

HCID 203341,3-Dimethylimidazolium IodideHCID 24758Sodium hydrideHCID 6453965Benzaldehyde, 3-(2-hydroxyethoxy)-HCID 220483501-Bromo-6,7-dimethoxyisoquinoline-4-carbonitrile

Product 1

HCID 695516881-(3-Hydroxyethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrileYield 48.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (11 mg, 0.26 mmol) was added to a stirred mixture of 1-Bromo-6,7-dimethoxy-isoquinoline-4-carbonitrile (see example 82) (50 mg, 0.17 mmol), 3-(2-hydroxyethoxy)-benzaldehyde (43 mg, 0.26 mmol), 1,3-dimethylimidazolium iodide (16 mg, 0.26 mmol) in DMF (2 mL). The reaction mixture became dark color. After 1 h, water (4 mL) was added to the above mixture, and extracted with chloroform (6 mL). The extract was washed with water (4 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford a solid. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 0–40% EtOAc in methylenechloride in 30 min) afforded 1-(3-hydroxyethoxy-benzoyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile (31 mg, 41%) as a white solid. LC-MS m/e calcd for C21H18N2O5 (MH+) 379, found 379.

Workup

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

Sources & evidence

ORD record
ord-895facc4a1424019a25f0bfe94deb690
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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