2-Methyl-8-nitroquinoline → 2-Methyl-8-aminoquinoline

HRID 1471287

Reaction equation

HRID 1471287 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([CH3:14])[CH:10]=[CH:9]2)([O-])=O>[Pd].C(O)C>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=2)[N:12]=1

Participants

4

Reactant 1

HCID 134332-Methyl-8-nitroquinoline

Product 1

HCID 1404572-Methyl-8-aminoquinolineYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a Pressure reaction bottle was added 5.0 g of 8-nitroquinaldine, 0.5 g 5% palladium on carbon, and 150 ml ethanol. The mixture was purged with hydrogen and then hydrogenated under 40 psi hydrogen for 16 hours. The catalyst was filtered off on a bed of celite. The solvent was removed, resulting in 4.2 g of a dark oil.

Workup

  1. customTo a Pressure reaction bottle
  2. customThe mixture was purged with hydrogen
  3. filtrationThe catalyst was filtered off on a bed of celite
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-666619a2067b430f9bdff3d037da84c0
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Linked notes

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