Acetic Acid → HCID 15485490, compound

HRID 369435Notes

Reaction equation

HRID 369435 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:10]([O:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[CH:42]=[CH:41][C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=3)[CH2:28][CH2:27]1)[C:9]2=[O:43])=[O:5])C.C(=O)([O-])O.[Na+].C(O)(=O)C>C(O)C>[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[C:10]([O:22][CH2:23][CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][N:29]([CH2:32][C:33]3[CH:42]=[CH:41][C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]=3)[CH2:30][CH2:31]1)[C:9]2=[O:43])([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 15485488HCID 15485488, compound

Product 1

HCID 15485490HCID 15485490, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Ethoxycarbonyl-3-[3-{4-(2-quinolinylmethyl)piperazin-1-yl}propoxy]flavone (0.8 mmol) was dissolved in 20 ml of ethanol, followed by the addition of 2 ml of a saturated aqueous solution of sodium hydrogencarbonate. The reaction mixture was refluxed for 2 hours and was then allowed to cool down. The solvent was driven off under reduced pressure. Acetic acid was added to the residue to neutralize the same, followed by extraction with chloroform. After the organic layer was concentrated under reduced pressure, the residue was recrystallized from EtOH-ether, whereby the title compound represented by the following formula was obtained (yield: 74%). ##STR67##

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperatureto cool down
  3. extractionfollowed by extraction with chloroform
  4. concentrationAfter the organic layer was concentrated under reduced pressure
  5. customthe residue was recrystallized from EtOH-ether, whereby the title compound
  6. customwas obtained (yield: 74%)

Sources & evidence

ORD record
ord-8b58d91ec32b4ff2a73a52a533b4df95
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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