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

HRID 1761877Notes

Reaction equation

HRID 1761877 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 206.8 kPa (30 p.s.i.) 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-728bfbfc867a4adbb757655b91e4b540
Source dataset
uspto-grants-1989_05
Patent number
US04829071

Reaction notes

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