Potassium Iodide → HCID 59807141, compound

HRID 1922509Notes

Reaction equation

HRID 1922509 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].C(=O)([O-])[O-].[K+].[K+].[CH3:25][NH:26][CH2:27][CH2:28][OH:29].[I-].[K+]>C(#N)C.O>[OH:29][CH2:28][CH2:27][N:26]([CH3:25])[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

7

Reactant 4

HCID 4875Potassium IodideHCID 80162-(Methylamino)ethanolHCID 11430Potassium CarbonateHCID 43446516HCID 43446516, compound

Product 1

HCID 59807141HCID 59807141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.861 mmol) and potassium carbonate (1286 mg, 9.30 mmol) in acetonitrile (5 ml) was added 2-(methylamino)ethanol (0.447 ml, 5.58 mmol). The resulting mixture was stirred overnight at room temperature under argon. The reaction mixture was then diluted with water and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed on silica gel using ethyl acetate as eluent, followed by 10% (2M NH3 in methanol) in dichloromethane. A large amount of starting material was recovered and resubjected to the reaction conditions, using potassium iodide, and heating overnight at 80° C. followed by workup and repurification.

Workup

  1. extractionextracted with dichloromethane (3×)
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel
  6. customA large amount of starting material was recovered
  7. customresubjected to the reaction conditions
  8. temperatureheating overnight at 80° C.
  9. customfollowed by workup and repurification

Sources & evidence

ORD record
ord-94fb0e786ead44a1b29242804ff2116c
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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