2-Methyl-6-nitroquinoline → 2-Methylquinolin-6-amine

HRID 467102

Reaction equation

HRID 467102 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=2)[N:3]=1>C(O)C.[Pd]>[NH2:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Participants

4

Reactant 1

HCID 691722-Methyl-6-nitroquinoline

Product 1

HCID 1031482-Methylquinolin-6-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-6-nitroquinoline (18.8 g) was stirred under a hydrogen atmosphere at 30 p.s.i. (equivalent to 206.8 kPa) for 2 hours in ethanol solution containing 5% Pd/C. The catalyst was then removed by filtration, the filtrate evaporated to small volume in vacuo, and the resultant precipitate collected by filtration, washed with ethanol and ether, and dried to give the title compound, yield 13.2 g, m.p. 188°-189°.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe filtrate evaporated to small volume in vacuo
  3. filtrationthe resultant precipitate collected by filtration
  4. washwashed with ethanol and ether
  5. customdried

Sources & evidence

ORD record
ord-3326914a57374ea28b33f529dd1a4a5f
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Linked notes

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