Diethyl Carbonate → HCID 85585358, compound

HRID 2232099Notes

Reaction equation

HRID 2232099 reaction equation
[C:1]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:20]([O:22][C:23](=O)[O:24]CC)[CH3:21]>C1C=CC=CC=1>[OH:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][C:9]=1[C:23]([O:22][CH2:20][CH3:21])=[O:24]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 10966127HCID 10966127, compound

Product 1

HCID 85585358HCID 85585358, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of 29 g of 2,3-dihydro-1-phenyl-4(1H)-quinolone in 200 ml of benzene was added, dropwise, to a stirred slurry of 7.2 g of sodium hydride in 200 ml of benzene. The slurry was stirred for one hour at room temperature, and then treated with 23.6 g of diethylcarbonate. The resulting suspension was refluxed for five hours, cooled to room temperature, and quenched with 200 ml of water. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and evaporated. Purification of the residue by means of high pressure liquid chromatography (silica gel; dichloromethane as the eluent) afforded 22.4 g (59%) of 1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxylic acid, ethyl ester. Recrystallization from diethyl ether yielded the analytical sample, m.p. 103°-106° C.

Workup

  1. temperatureThe resulting suspension was refluxed for five hours
  2. temperaturecooled to room temperature
  3. customquenched with 200 ml of water
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by means of high pressure liquid chromatography (silica gel

Sources & evidence

ORD record
ord-11a785548adc492fb1a5075c0028fbe0
Source dataset
uspto-grants-1988_11
Patent number
US04786644

Reaction notes

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