5-Fluoroquinolin-8-amine → 5-Fluoro-1,2,3,4-tetrahydroquinolin-8-amine

HRID 243201Notes

Reaction equation

HRID 243201 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH2:6][NH:7]2.FC1C=CC(N)=C2C=1C=CC=N2>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][NH:7]2

Participants

5

Reactant 2

HCID 445582645-Fluoroquinolin-8-amineHCID 68157725HCID 68157725, compound

Product 1

HCID 681575905-Fluoro-1,2,3,4-tetrahydroquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoro-8-nitro-1,2-dihydroquinoline (83.6 mg, 0.43 mmol) in EtOAc (10 mL) was added a slurry of 10% Pd/C (28 mg) in IMS (3 mL) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 22 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo affording a mixture of the title compound and 5-fluoroquinolin-8-ylamine as a purple oil (70.4 mg, 99%). 1H NMR (CDCl3, 300 MHz) (signals due to title compound): 6.46 (1H, dd, J=8.5, 5.5 Hz), 6.28 (1H, dd, J=9.2, 8.5 Hz), 3.31-3.28 (2H, m), 3.24 (3H, bs), 2.72 (2H, t, J=6.5 Hz), 1.94-1.86 (2H, m)

Workup

  1. filtrationThe suspension was then filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. customaffording

Sources & evidence

ORD record
ord-dc944810b04c4fc09ccc478d132ef563
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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