Sodium Cyanide → HCID 22048415, compound

HRID 1833250Notes

Reaction equation

HRID 1833250 reaction equation
[CH:1]([O:5][C:6]1[CH:7]=[C:8]([CH:26]=[CH:27][CH:28]=1)[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([CH2:24]Cl)=[CH:12][N:11]=1)([CH2:3][CH3:4])[CH3:2].[C-:29]#[N:30].[Na+].C(OCC)(=O)C.CCCCCC>CS(C)=O.C(OCC)(=O)C.O>[CH:1]([O:5][C:6]1[CH:7]=[C:8]([CH:26]=[CH:27][CH:28]=1)[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=2)[C:13]([CH2:24][C:29]#[N:30])=[CH:12][N:11]=1)([CH2:3][CH3:4])[CH3:2]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 21226206Ethyl acetate hexaneHCID 22048335HCID 22048335, compound

Product 1

HCID 22048415HCID 22048415, compoundYield 91.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-(3-sec-butoxy-benzyl)-4-chloromethyl-6,7-dimethoxy-isoquinoline (950 mg, 2.38 mmol) in methyl sulfoxide (10 mL) was added sodium cyanide (582, 11.9 mmol). The reaction mixture was stirred at room temperature for 1 h and diluted with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (3×25 mL). The combined extracts were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 40% ethyl acetate/hexane) afforded [1-(3-sec-butoxy-benzyl)-6,7-dimethoxy-isoquinolin-4-yl]-acetonitrile (850 mg, 91% yield) as a colorless oil.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (3×25 mL)
  2. washThe combined extracts were washed with saturated aqueous sodium chloride solution (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d971729a1094f2db3eeafd2fd9672b8
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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