6-Methoxy-8-nitroquinoline → 6-Methoxy-8-quinolinamine

HRID 513376Notes

Reaction equation

HRID 513376 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N+:13]([O-])=O)[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.O.NN>[Ni].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH2:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 2

HCID 68226-Methoxy-8-nitroquinolineHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 70236-Methoxy-8-quinolinamineYield 102.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Raney Nickel (60 mg, 20% wt) was added portionwise to a solution of 6-methoxy-8-nitroquinoline (300 mg, 1.40 mmol) in MeOH (10 ml), under argon. Hydrazine hydrate (270 μl, 5.6 mmol) was added and the reaction stirred at room temperature for 1 h. The mixture was filtered through celite and washed with MeOH. The filtrate was concentrated in vacuo, re-dissolved in DCM and washed with water. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound (250 mg, 100%) which was used in the next step without purification.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionre-dissolved in DCM
  5. washwashed with water
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52814854c9b440a993e11feb1980c3c5
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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