Sodium Iodide → HCID 22048334, compound

HRID 1833114Notes

Reaction equation

HRID 1833114 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([CH2:21]Cl)=[CH:9][N:8]=1.[C-:26]#[N:27].[Na+].[I-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([CH2:21][C:26]#[N:27])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 22048373HCID 22048373, compound

Product 1

HCID 22048334HCID 22048334, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above 1-(3-methoxybenzyl)-4-chloromethyl-6,7-dimethoxyisoquinoline (361 mg, 1.0 mmol) was suspended into 15 ml of 90% ethanol. Then sodium cyanide (392 mg, 8.0 mmol) and sodium iodide (83 mg, 0.5 mmol) was added. The mixture was refluxed for 4 hrs. solvents were evaporated and the residue was extracted with ethyl acetate. After the evaporation of solvents, the residue was purified by flash column chromatography using ethyl acetate and hexane (2/1) to give 1-(3-methoxybenzyl)-4-cyanomethyl-6,7-dimethoxyisoquinoline as a solid (165 mg, 47.4%). ES-MS calculated for C21H20O3N2 (m/e) 348.41, observed 349.5.5 (M+1). 1H-NMR is consistent with the desired structure.

Workup

  1. temperatureThe mixture was refluxed for 4 hrs
  2. customsolvents were evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. customAfter the evaporation of solvents
  5. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-bf22dfee0704442ea125f421bab8047c
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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