2-(8-Fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamine → 1-(2-(Dimethylamino)ethyl)-8-fluoro-1,2,3,4-tetrahydroquinolin-6-amine

HRID 1922435Notes

Reaction equation

HRID 1922435 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:17]([O-])=O)[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[CH2:9][CH2:8][CH2:7]2.[H][H]>[Pd].C(O)C>[CH3:15][N:14]([CH3:16])[CH2:13][CH2:12][N:10]1[C:11]2[C:6](=[CH:5][C:4]([NH2:17])=[CH:3][C:2]=2[F:1])[CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 533922632-(8-Fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 533923481-(2-(Dimethylamino)ethyl)-8-fluoro-1,2,3,4-tetrahydroquinolin-6-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(8-Fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamine (340 mg, 1.27 mmol) was weighed into a round bottom flask equipped with a stir bar. Ethanol (8 mL) was added, followed by Pd (10 wt. % on activated carbon). The flask was fitted with a balloon of hydrogen, evacuated of air and backfilled with hydrogen. The reaction mixture was stirred for 2 h at room temperature under balloon pressure. The reaction mixture was then filtered through a pad of celite and the pad washed with methanol. The filtrate was concentrated, then chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in dichloromethane. Yield: 270 mg, 89%. ESI-MS: 238 (MH+, 100), 193 (37), 147 (31).

Workup

  1. customequipped with a stir bar
  2. customevacuated of air
  3. filtrationThe reaction mixture was then filtered through a pad of celite
  4. washthe pad washed with methanol
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on silica gel using 0-10% (2M NH3 in MeOH) in dichloromethane

Sources & evidence

ORD record
ord-6c8deb1a3ff94777a5680b8a4abf21df
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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