6-Nitroquinoline → 6-Aminoquinoline

HRID 549260Notes

Reaction equation

HRID 549260 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 1

HCID 119456-Nitroquinoline

Product 1

HCID 113736-AminoquinolineYield 457.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 6-nitro-quinoline (8.7 g, 5 mmol), palladium on charcoal (10%) (0.1 g) in methanol (0.2 L) was hydrogenated at room temperature for 24 with stirring. The catalyst was filtered and the solvent evaporated to yield a yellow solid. Crystallisation from ethyl acetate yielded the pure title compound as a pale yellow solid (3.3 g, 46%). MS m/z: 145 [M+H+]. 1H NMR (270 MHz, CHCl3-d) δ ppm 3.89 (s, 2H) 6.87 (d, J=2.64 Hz, 1H) 7.14 (dd, J=8.97, 2.64 Hz, 1H) 7.25 (dd, J=8.44, 4.22 Hz, 1H) 7.88 (dd, J=7.92, 1.58 Hz, 1H) 7.90 (d, J=8.97 Hz, 1H) 8.63 (dd, J=4.22, 1.58 Hz, 1H).

Workup

  1. customwas hydrogenated at room temperature for 24
  2. filtrationThe catalyst was filtered
  3. customthe solvent evaporated
  4. customto yield a yellow solid
  5. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-8e9c3889a28f4285ade58c6725a3880b
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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