2-Methoxy-8-nitroquinoline → 2-Methoxyquinolin-8-amine

HRID 2306256Notes

Reaction equation

HRID 2306256 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([N+:13]([O-])=O)[CH:7]=[CH:8][CH:9]=2)[N:4]=1>CCO>[NH2:13][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11]2

Participants

3

Reactant 1

HCID 184336082-Methoxy-8-nitroquinoline

Product 1

HCID 4368672-Methoxyquinolin-8-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methoxy-8-nitroquinoline, as described above in Step D, (2.07 g, 10.14 mmol) was dissolved in EtOH (150 mL) and EtOAc (150 mL), the vessel was degassed, Pd/C (200 mg, 10 wt %) was added and the vessel was filled with H2 (1 atm). After 1 hour, the reaction was filtered through a pad of celite and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with CH2Cl2, to yield the above-titled compound.

Workup

  1. customEtOAc (150 mL), the vessel was degassed
  2. additionPd/C (200 mg, 10 wt %) was added
  3. additionthe vessel was filled with H2 (1 atm)
  4. filtrationthe reaction was filtered through a pad of celite
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel
  7. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-fe683297d3d141d5af1890da04c757d9
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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