Water → HCID 59807104, compound

HRID 1922374Notes

Reaction equation

HRID 1922374 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].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23](=[O:25])[CH3:24].O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:22][C:23](=[O:25])[CH3:24])[C:9](=[O:14])[CH2:8][CH2:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 51117496-Nitro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 59807104HCID 59807104, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-nitro-3,4-dihydroquinolin-2(1H)-one (950 mg, 4.94 mmol) and potassium carbonate (4.10 g, 29.64 mmol) in 12 mL DMF was treated with chloroacetone (787 μL, 9.89 mmol) and stirred at room temperature overnight. After this time, the mixture was cooled to 0° C. and treated with 50 mL H2O under rapid stirring. A precipitate formed and it was filtered then washed with 50 mL H2O. The solid was collected and dried under reduced pressure overnight (1.01 g, 82.1%). 1H-NMR (DMSO-d6) δ: 8.17 (d, J=2.4 Hz, 1H), 8.05 (dd, J=2.4, 8.7 Hz, 1H), 7.05 (d, J=8.7 Hz, 1H), 3.33 (s, 2H), 3.05 (t, J=7.8 Hz, 2H), 2.66 (t, J=7.8 Hz, 2H), 2.24 (s, 3H). MS (EI): 248 (M+).

Workup

  1. temperatureAfter this time, the mixture was cooled to 0° C.
  2. customA precipitate formed
  3. filtrationit was filtered
  4. washthen washed with 50 mL H2O
  5. customThe solid was collected
  6. customdried under reduced pressure overnight (1.01 g, 82.1%)

Sources & evidence

ORD record
ord-b65d5e30a7d64ef5933fa24eedb6cf19
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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