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

HRID 1922364Notes

Reaction equation

HRID 1922364 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2].Cl.Cl[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][N:10]1[C:11]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=2)[CH2:7][CH2:8][C:9]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-oneHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 533920911-(2-(dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-oneYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (1.5 g, 7.80 mmol), 2-chloro-N,N-dimethylethanamine hydrochloride (2.25 g, 15.60 mmol) and potassium carbonate (6.47 g, 46.80 mmol) in 25 mL DMF was stirred at room temperature for 3 days. After this time, the mixture was poured into 20 mL H2O then extracted with 3×150 mL EtOAc. The combined organic fractions were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a yellow viscous oil (1.5 g, 73.2%). 1H-NMR (CDCl3) δ: 8.14 (dd, J=2.4, 9.0 Hz, 1H), 8.06 (d, J=2.4 Hz, 1H), 7.15 (d, J=9.0 Hz, 1H), 4.09 (t, J=7.5 Hz, 2H), 3.03-2.98 (m, 2H), 2.73-2.68 (m, 2H), 2.51 (t, J=7.5 Hz, 2H), 2.31 (s, 6H).

Workup

  1. extractionthen extracted with 3×150 mL EtOAc
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-efad7139bcf145fd9b0af63df730d279
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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