Potassium Carbonate → (R)-5-Dipropylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 1792098Notes

Reaction equation

HRID 1792098 reaction equation
[CH2:1]([NH:4][C@@H:5]1[CH2:14][C:13]2[C:8]3=[C:9]([N:15]([O:18][CH3:19])[C:16](=[O:17])[N:7]3[CH2:6]1)[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH3:3].I[CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[C@@H:5]1[CH2:14][C:13]2[C:8]3=[C:9]([N:15]([O:18][CH3:19])[C:16](=[O:17])[N:7]3[CH2:6]1)[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-Iodopropane2×HCID 10286043HCID 10286043, compound

Product 1

HCID 9817922(R)-5-Dipropylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the procedure of Example 3, a mixture of (R)-5-Propylamino-1-methoxy-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (8b, 0.93 g, 3.56 mmol), 1-iodopropane (3.05 g, 17.9 mmol), and potassium carbonate (1.97 g, 14.3 mmol) in acetonitrile (25 ml) was heated at reflux under nitrogen for 17 hours. 1-Iodopropane (3.05 g, 17.9 mmol) was again added, and the mixture was refluxed for an additional 5 hours. The solvent was removed under vacuum, and the mixture was diluted with water and extracted twice with diethylether. The organic extract was washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave an amber oil. Purification by flash chromatography (230–400 mesh silica gel; 10–25% ethyl acetate in hexane) gave the title compound (9b) as an amber oil (0.87 g, 90% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 17 hours
  3. temperaturethe mixture was refluxed for an additional 5 hours
  4. customThe solvent was removed under vacuum
  5. additionthe mixture was diluted with water
  6. extractionextracted twice with diethylether
  7. extractionThe organic extract
  8. washwas washed with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent was removed under vacuum
  11. customto leave an amber oil
  12. customPurification by flash chromatography (230–400 mesh silica gel; 10–25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d343a18f0d5d4b3e83df4a271cf4b5d1
Source dataset
uspto-grants-2006_07
Patent number
US07074927B2

Reaction notes

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