1-(2-(dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one → HCID 43446585, compound

HRID 1922365Notes

Reaction equation

HRID 1922365 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-])=O)=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:18].[H][H]>[Pd].C(O)C>[NH2:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:19])[C:6](=[O:18])[CH2:7][CH2:8]2

Participants

5

Reactant 2

HCID 533920911-(2-(dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 43446585HCID 43446585, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-(2-(dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (1.48 g, 5.62 mmol) and palladium on activated carbon (10%, 300 mg, 0.28 mmol) in 20 mL ethanol was stirred under a balloon of hydrogen overnight. The suspension was filtered through a pad of celite. The filter pad was rinsed with 50 mL ethanol and the filtrate was concentrated to give a viscous oil. The crude product was used without further purification. (1.3 g, 100%). 1H-NMR (CDCl3) δ: 6.85 (d, J=8.7 Hz, 1H), 6.55 (dd, J=2.7, 8.7 Hz, 1H), 6.51 (d, J=2.7 Hz, 1H), 4.00 (t, J=7.5 Hz, 2H), 3.56 (br s, 2H), 2.80-2.75 (m, 2H), 2.60-2.55 (m, 2H), 2.47 (t, J=7.5 Hz, 2H), 2.31 (s, 6H).

Workup

  1. filtrationThe suspension was filtered through a pad of celite
  2. washThe filter pad was rinsed with 50 mL ethanol
  3. concentrationthe filtrate was concentrated
  4. customto give a viscous oil
  5. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-66b28c8834d24805b041207400cfe33c
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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