Methanol → HCID 11196248, compound

HRID 639897Notes

Reaction equation

HRID 639897 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([C:20]#[N:21])[N:3]=1.CO.[H][H]>[Pd].[O-]S([O-])(=O)=O.[Ba+2].C(Cl)Cl>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH:2]=[N:3][C:4]([C:20]#[N:21])=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 114264141-Chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 11196248HCID 11196248, compound

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-chloro-6-methoxy-4-phenylisoquinoline-3-carbonitrile (200 mg), 5% Pd/BaSO4 (50 mg), and 20 mL methanol was stirred under 1 atm hydrogen for 18 h. 5 mL of CH2Cl2 was then added, as was an additional 50 mg Pd/BaSO4. After stirring overnight, the reaction was filtered, concentrated, and purified by flash chromatography (30% EtOAc/hexanes) to give the titled compound.

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated
  3. custompurified by flash chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-21122a785cfe4cf4b7c43b8448b56566
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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