4-Chloro-8-nitroquinoline → 8-Aminoquinoline

HRID 1469778Notes

Reaction equation

HRID 1469778 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[NH2:12])[CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 6104404-Chloro-8-nitroquinoline

Product 1

HCID 113598-AminoquinolineYield 48.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-8-nitroquinoline (Intermediate-11, step-2, 150 mg, 0.71 mmol) in EtOAc (3 mL) was added 10% Pd on C (75 mg) and the suspension was hydrogenated in a Parr apparatus for 4 h at 20 psi. Then the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by column chromatography using 10% EtOAc in CHCl3 to afford 50 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.71 (d, 1H), 8.17 (d, J=8.4 Hz, 1H), 7.47-7.43 (m, 1H), 7.28 (t, J=7.8 Hz, 1H), 7.05 (d, J=8.4 Hz, 1H), 6.86 (d, J=7.2 Hz, 1H), 5.90 (s, 2H).

Workup

  1. filtrationThen the reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3c5de2a02f204bc29e9f994e5dc6370b
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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