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

HRID 2102964Notes

Reaction equation

HRID 2102964 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>[Pd].CO>[NH2:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([CH3:1])[N:3]=[CH:4]2

Participants

4

Reactant 1

HCID 2749733-Methyl-5-nitroisoquinoline

Product 1

HCID 122120553-Methylisoquinolin-5-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-methyl-5-nitroisoquinoline (1.3 g, 0.0069 mol—prepared according to the procedure in WO 2004/024710), 10% Pd—C (100 mg) and MeOH (100 mL) was stirred under an atmosphere of hydrogen (1 atm) at rt for 2 h. The mixture was filtered and the filtrate was concentrated under vacuum to give a light yellow solid (1.1 g, 100%). LC-MS: 0.64 min, 159.1 (M+1).

Workup

  1. customprepared
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-0f3d1623ffc543dea35c7ccbf12c2bc3
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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