3-Methyl-5-nitroisoquinoline → 3-Methylisoquinolin-5-amine

HRID 1181405Notes

Reaction equation

HRID 1181405 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-])=O)[CH:8]=[CH:7][CH:6]=2.[H][H]>CO.O=[Pt]=O>[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:12])[C:10]=2[CH:11]=1

Participants

5

Reactant 2

HCID 2749733-Methyl-5-nitroisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 122120553-Methylisoquinolin-5-amineYield 45%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

3-Methyl-5-nitroisoquinoline (Description 44; 660 mg, 3.51 mmol) was dissolved in MeOH (30 ml) and PtO2 catalyst (120 mg) was added. The mixture was stirred for 1 hour 45 minutes under a balloon of hydrogen, then the catalyst was filtered off, washing with more methanol. The filtrate was evaporated and purified by flash column chromatography using as eluant 5% methanol in dichloromethane to give the title compound (250 mg).

Workup

  1. filtrationthe catalyst was filtered off
  2. washwashing with more methanol
  3. customThe filtrate was evaporated
  4. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-25239c1579fe494cb14a82982b8855b3
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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