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

HRID 407115Notes

Reaction equation

HRID 407115 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]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:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2](=[O:1])[CH2:3][CH2:4]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

5.04 g of 4-oxo-1,2,3,4-tetrahydroquinoline was dissolved in 20 mL of tetrahydrofuran at 25° C. 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 the mixture was stirred at 25° C. for 24 hours. To the reaction solution was added ethyl acetate, and the organic layer was separated, dried over magnesium sulfate, and then filtered. The filtrate was concentrated and the residue was dissolved in 35 mL of isopropyl alcohol under heating. The solution was cooled gradually, and the precipitated crystals were collected by filtration under ice-cooled condition. The resulting crystals were washed with 25 mL of cold isopropyl alcohol, and then dried at 50° C. for 16 hours to give 8.98 g of 1-benzyloxycarbonyl-4-oxo-1,2,3,4-tetrahydroquinoline (93% yield).

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue was dissolved in 35 mL of isopropyl alcohol
  7. temperatureunder heating
  8. temperatureThe solution was cooled gradually
  9. filtrationthe precipitated crystals were collected by filtration under ice-
  10. temperaturecooled condition
  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-7300d0181bf14fc4bbc2ad28f662d6bf
Source dataset
uspto-grants-2014_06
Patent number
US08754221B2

Reaction notes

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