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

HRID 1922340Notes

Reaction equation

HRID 1922340 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.[CH3:16][N:17]([CH2:19][CH2:20]Cl)[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH3:16][N:17]([CH3:18])[CH2:19][CH2:20][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

7

Reactant 3

HCID 11430Potassium Carbonate2×HCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-oneHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride2×

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 2.60 mmol), (N,N-dimethylamino)ethyl chloride hydrochloride (412 mg, 2.86 mmol) and potassium carbonate (1.07 g, 7.74 mmol) in 8 mL DMF was stirred at room temperature for 48 hours. Additional (N,N-dimethylamino)ethyl chloride hydrochloride (187 mg, 1.30 mmol) and potassium carbonate (359 mg, 2.60 mmol). Reaction was stirred for an additional 16 hours. After this time, the reaction was transferred to a separatory funnel and diluted with cold water and ethyl acetate. The aqueous was extracted twice more with ethyl acetate and 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 solid. Yield: 370 mg (54%). 1H NMR (CDCl3) δ: 8.15 (dd, J=2.7, 9.0 Hz, 1H), 8.06 (d, J=2.7 Hz, 1H), 7.17 (d, J=9 Hz, 1H), 4.09 (t, J=7.2 Hz, 2H), 3.00 (t, J=6.6 Hz, 2H), 2.71 (t, J=7.5 Hz, 2H), 2.52 (t, J=7.5 Hz, 2H), 2.32 (s, 6H). MS (ESI): 264.1 (M+1).

Workup

  1. customReaction
  2. stirringwas stirred for an additional 16 hours
  3. customAfter this time, the reaction was transferred to a separatory funnel
  4. extractionThe aqueous was extracted twice more with ethyl acetate
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a yellow solid

Sources & evidence

ORD record
ord-7a6f60e1013247ee9db68dc1099cda5e
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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