Potassium Iodide → HCID 53392258, compound

HRID 1922344Notes

Reaction equation

HRID 1922344 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:18].Cl.[CH3:20][NH:21][CH3:22].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][N:21]([CH3:22])[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:18]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 43446516HCID 43446516, compound

Product 1

HCID 53392258HCID 53392258, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (300 mg, 1.12 mmol), dimethylamine hydrochloride (911 mg, 11.16 mmol), potassium iodide (1.85 g, 11.16 mmol) and potassium carbonate (1.54 g, 11.16 mmol) were weighed into an argon purged vial fitted with a magnetic stirbar. Anhydrous acetonitrile was added, and the yellow suspension stirred at room temperature for 18 hours. The reaction was placed in a heating block at a temperature of 60° C. for 2 hours. After cooling to room temperature, the reaction was filtered through celite and the celite pad washed with methanol and the filtrate concentrated to afford a yellow solid. No further purification was performed. Yield: 520 mg crude material. 1H NMR (DMSO) δ: 8.11 (d, J=2.4 Hz, 1H), 8.06 (dd, J=2.7 Hz, 9.3 Hz, 1H), 7.41 (d, J=9 Hz, 1H), 3.94 (t, J=7.2 Hz, 2H), 2.99 (t, J=6.9 Hz, 2H), 2.73 (s, 6H), 2.59 (t, J=8.1 Hz, 2H), 2.45 (t, J=1.5 Hz, 2H), 1.86 (t, J=7.5 Hz, 2H). MS (ESI): 278.1 (M+1).

Workup

  1. customvial fitted with a magnetic stirbar
  2. waitThe reaction was placed in a heating block at a temperature of 60° C. for 2 hours
  3. temperatureAfter cooling to room temperature
  4. filtrationthe reaction was filtered through celite
  5. washthe celite pad washed with methanol
  6. concentrationthe filtrate concentrated
  7. customto afford a yellow solid
  8. customNo further purification

Sources & evidence

ORD record
ord-c77f8e3af2e4456d8bb1e4366ebf3b78
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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