Dichloromethane → HCID 89813171, compound

HRID 1481059Notes

Reaction equation

HRID 1481059 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](I)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH3:24])[CH:9]=2)=[O:4].[Cu](C#N)[C:27]#[N:28].ClCCl>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:27]#[N:28])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][CH3:24])[CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 89812849HCID 89812849, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 89813171HCID 89813171, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-(2-Ethyl-phenoxy)-4-hydroxy-1-iodo-isoquinoline-3-carboxylic acid methyl ester (1.5 g, 3.34 mmole) and copper cyanide (598 ml, 6.68 mmole) in anhydrous dimethylformamide (13 ml) was refluxed for 5 minutes before it was cooled to room temperature and dichloromethane was added and stirred for 5 minutes. The suspension was filtered. The filtrate was washed with 0.1 N HCl, twice with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was recrystallized with acetonitrile. The crystal was filtered and dried to give the title compound as a white solid (902 mg): MS: (+) m/z 349.08 (M+1), (−) m/z 347.10 (M−1).

Workup

  1. temperaturewas refluxed for 5 minutes before it
  2. filtrationThe suspension was filtered
  3. washThe filtrate was washed with 0.1 N HCl, twice with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized with acetonitrile
  7. filtrationThe crystal was filtered
  8. customdried

Sources & evidence

ORD record
ord-b5347073dc7745ceb801b3e66e80e51a
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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