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

HRID 345041

Reaction equation

HRID 345041 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-11ff7ed9f41c4091876e3ffef802b25a
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Linked notes

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