Ethanol → 6-Amino-1-(2-(dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one

HRID 1922432Notes

Reaction equation

HRID 1922432 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:16]([O-])=O)=[CH:12][C:13]=2[F:15])[CH2:8][CH2:7][C:6]1=[O:19].C(O)C.[H][H]>[Pd].C1COCC1>[NH2:16][C:11]1[CH:10]=[C:9]2[C:14](=[C:13]([F:15])[CH:12]=1)[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:20])[C:6](=[O:19])[CH2:7][CH2:8]2

Participants

6

Reactant 3

HCID 702EthanolHCID 533921801-(2-(Dimethylamino)ethyl)-8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 533921846-Amino-1-(2-(dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-(Dimethylamino)ethyl)-8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.77 mmol) was weighed into a round bottom flask equipped with a stirbar. Ethanol (10 mL) and THF (2 mL) were 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 black suspension was stirred for 3 h at room temperature. The solid palladium was then filtered off through a plug of celite and the celite pad washed with methanol. The filtrate was concentrated, then chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in ethyl acetate to give the product. Yield: 325 mg, 72%. EI-MS: 251 (M+, 3), 58 (100).

Workup

  1. customequipped with a stirbar
  2. customevacuated of air
  3. filtrationThe solid palladium was then filtered off through a plug of celite
  4. washthe celite pad washed with methanol
  5. concentrationThe filtrate was concentrated
  6. customchromatographed on silica gel using 0-10% (2M NH3 in MeOH) in ethyl acetate
  7. customto give the product

Sources & evidence

ORD record
ord-1055b6d39cbd45459f4383aeb05493c4
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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