5-Fluoro-2-methyl-8-nitro-1,2-dihydroquinoline → 5-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-amine

HRID 243214Notes

Reaction equation

HRID 243214 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][CH:6]([CH3:15])[NH:7]2.FC1C=CC(N)=C2C=1C=CC(C)=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][CH:6]([CH3:15])[NH:7]2

Participants

5

Reactant 2

HCID 681574055-Fluoro-2-methyl-8-nitro-1,2-dihydroquinolineHCID 681578245-Fluoro-2-methylquinolin-8-amine

Product 1

HCID 681578015-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolin-8-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of 10% Pd/C (30 mg) in a mixture of IMS (3 mL) and EtOAc (5 mL) was stirred under an atmosphere of hydrogen for 15 min before a solution of 5-fluoro-2-methyl-8-nitro-1,2-dihydroquinoline (76.8 mg, 0.369 mmol) in EtOAc (15 mL) was added. The reaction mixture was stirred at RT under a hydrogen atmosphere for 20 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-fluoro-2-methylquinolin-8-ylamine as a purple oil. LCMS (Method J): RT 1.90 min (28%) [M+H]+ 181 and 2.26 min (42%) [M+H]+ 177

Workup

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

Sources & evidence

ORD record
ord-4c13171b37bc4bc99f1057ba52ace06d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…