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

HRID 1922410Notes

Reaction equation

HRID 1922410 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+]>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

5

Reactant 3

HCID 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)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Nitro-3,4-dihydroquinolin-2(1H)-one (5 g, 25.61 mmol) and 2-chloro-N,N-dimethylethanamine hydrochloride (7.38 g, 51.23 mmol) were weighed into a round bottom flask and stirred in DMF (50 mL). To this solution/suspension was added potassium carbonate (21.59 g, 156.2 mmol). The resulting suspension was stirred overnight at room temperature. The reaction mixture was then poured into ice water (150 mL) and extracted with ethyl acetate (2×100 mL). The combined organics were washed with water (1×) and brine (1×). The organic phase was dried over sodium sulfate, filtered and concentrated. The resulting residue was chromatographed in 0-20% (2M NH3 in MeOH) in 1:1 dichloromethane and ethyl acetate, giving a yellow solid. Yield: 5.8 g, 84%. 1H NMR (CDCl3) δ 8.14 (dd, 1H, J=9.0, 3.0 Hz) 8.06 (d, 1H, J=3.0 Hz), 7.16 (d, 1H, J=9.0 Hz), 4.08 (t, 1H, J=7.5 Hz), 3.00 (t, 1H, J=7.5 Hz), 2.70 (t, 1H, J=7.5 Hz); 2.51 (t, 1H, J=7.5 Hz), 2.31 (s, 6H).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe combined organics were washed with water (1×) and brine (1×)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was chromatographed in 0-20% (2M NH3 in MeOH) in 1:1 dichloromethane and ethyl acetate
  7. customgiving a yellow solid

Sources & evidence

ORD record
ord-877985112495481e8a582662d0305cbe
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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