HCID 69522925, compound → HCID 69522791, compound

HRID 1181422Notes

Reaction equation

HRID 1181422 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:12])[N:8]=[CH:9]2)=[C:4]([N+:13]([O-])=O)[CH:3]=1.[H][H]>CO.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]2[CH:6]=[C:7]([CH3:12])[N:8]=[CH:9][C:10]=2[CH:11]=1

Participants

6

Reactant 2

HCID 69522925HCID 69522925, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69522791HCID 69522791, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

To a nitrogen flushed solution of 7-chloro-3-methyl-5-nitroisoquinoline (Description 85; 300 mg, 1.35 mmol) in methanol (30 ml) was added a spatula end of Palladium 5% on calcium carbonate poisoned with lead (lindlar catalyst), and the resulting mixture stirred under a balloon of hydrogen overnight. The catalyst was removed by filtration and the filtrate evaporated. The residue was dissolved in methanol (20 ml) and silica gel (2 g) added and evaporated to dryness. Loaded onto a silica gel column and eluted with 1% MeOH in DCM+0.5% NH4OH to give the title compound (190 mg, 73%) as an orange solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in methanol (20 ml)
  4. additionsilica gel (2 g) added
  5. customevaporated to dryness
  6. washLoaded onto a silica gel column and eluted with 1% MeOH in DCM+0.5% NH4OH

Sources & evidence

ORD record
ord-0738e302be4c45759f4e74790e1fd1f4
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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