Water → Benzyl 4-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 252239Notes

Reaction equation

HRID 252239 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[CH2:12]([O:19][C:20]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 1171582,3-dihydroquinolin-4(1H)-one

Product 1

HCID 23726243Benzyl 4-oxo-3,4-dihydroquinoline-1(2H)-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

In 20 mL of tetrahydrofuran was dissolved 5.04 g of 2,3-dihydro-4-quinolone at 25° C., then, to the solution were added 5.6 mL of benzyloxycarbonyl chloride, 15 mL of water and 4.73 g of potassium carbonate under ice-cooling, and said mixture was stirred at 25° C. for 24 hours. Ethyl acetate was added to the reaction mixture, and the organic layer was separated, dried over anhydrous magnesium sulfate, and then, filtered. The filtrate was concentrated, and the residue was dissolved in 35 mL of isopropyl alcohol under heating. Said solution was gradually cooled, and the precipitated crystals were collected by filtration under ice-cooling. The resulting crystals were washed with 25 mL of cold isopropyl alcohol, and dried at 50° C. for 16 hours to obtain 8.98 g (Yield: 93%) of 1-benzyloxycarbonyl-2,3-dihydro-4-quinolone.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue was dissolved in 35 mL of isopropyl alcohol
  7. temperatureunder heating
  8. temperaturewas gradually cooled
  9. filtrationthe precipitated crystals were collected by filtration under ice-
  10. temperaturecooling
  11. washThe resulting crystals were washed with 25 mL of cold isopropyl alcohol
  12. customdried at 50° C. for 16 hours

Sources & evidence

ORD record
ord-ba7be18c10704afeafa9837b3d684b63
Source dataset
uspto-grants-2011_01
Patent number
US07868019B2

Reaction notes

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