Citric Acid → 6-(2-carboxyphenyl)methoxy-5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 341841Notes

Reaction equation

HRID 341841 reaction equation
C(O)C.C[O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][CH:16]1[C:25]2[C:20]3=[C:21]([N:26]=[C:27]([CH2:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:19]3[CH2:18][CH2:17]1)[CH:22]=[CH:23][CH:24]=2)=[O:7].[OH-].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][O:15][CH:16]1[C:25]2[C:20]3=[C:21]([N:26]=[C:27]([CH2:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:19]3[CH2:18][CH2:17]1)[CH:22]=[CH:23][CH:24]=2)([OH:7])=[O:5]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 158384695,6-dihydro-6-(2-methoxycarbonylphenyl)methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 675961586-(2-carboxyphenyl)methoxy-5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolineYield 61.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethanol (4 mL) was added to 0.62 g of the 5,6-dihydro-6-(2-methoxycarbonylphenyl)methoxy-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline obtained in Example 19; to the solution, another solution having potassium hydroxide (0.19 g) dissolved in water (0.4 mL) was added and the mixture was heated under reflux for 1 hr. After standing to cool, the reaction solution was poured into water and its pH was adjusted to 4-5 using 10% aqueous citric acid; after extraction with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate) to yield the titled compound as pale yellow crystals (0.37 g).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hr
  4. temperatureto cool
  5. extractionafter extraction with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-9b1678ad323e492c9630d72054475c61
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

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