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

HRID 1031981Notes

Reaction equation

HRID 1031981 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-b4b78fec080248f3b94b7b3a9e575e16
Source dataset
uspto-grants-1990_09
Patent number
US04956382

Reaction notes

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