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

HRID 987571Notes

Reaction equation

HRID 987571 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>[Pd].C1COCC1>[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

4

Reactant 1

HCID 68226-Methoxy-8-nitroquinoline

Product 1

HCID 70236-Methoxy-8-quinolinamineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 9.20 g (45.1 mmol) 6-methoxy-8-nitroquinoline, 1.8 g of 10% Pd/C and 150 mL THF is placed under 40 psi of H2 and shaken in a Parr reactor at 23° C. for 4 h. The Pd/C is removed via filtration through celite, and the solvent evaporated. Flash chromatography on SiO2 gel, eluting with hexanes/EtOAc (1/1 to 1/3), gives 7.40 g (42.5 mmol, a 95% yield) of the title compound as an off-white solid. MS (ES) m/z 175 (MH)+.

Workup

  1. customThe Pd/C is removed via filtration through celite
  2. customthe solvent evaporated
  3. washFlash chromatography on SiO2 gel, eluting with hexanes/EtOAc (1/1 to 1/3)
  4. customgives 7.40 g (42.5 mmol

Sources & evidence

ORD record
ord-c1c42ae3f990462db8894526e6434935
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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