Water → HCID 68540953, compound

HRID 1985087Notes

Reaction equation

HRID 1985087 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][C:6]2=[O:13])[CH3:2].C(=O)(O)[O-].[Na+].O.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH2:8][CH2:7][C:6]2=[O:13])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate2×HCID 223244436-Ethyl-2,3-dihydroquinolin-4(1H)-one

Product 1

HCID 68540953HCID 68540953, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-ethyl-2,3-dihydroquinolin-4(1H)-one (1.25 g) in THF (15 mL) was added sodium bicarbonate (0.84 g). Water (5 mL) followed by benzyl chloroformate (1.58 g) were added to the mixture,and it was stirred at room temperature overnight. The reaction was not complete as determined by TLC, so an additional 0.60 g of NaHCO3 were added to the mixture and it was stirred at room temperature for two additional hours. The mixture was then concentrated under reduced pressure and the residue was partitioned between water and ethyl acetate and the organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated. Chromotography on silicia gel using 25% ethyl acetate in heptane solvent solution gave 1.84 g of the title compound. MS (ESI+) for C19H19NO3 m/z 310.03 (M+H)+.

Workup

  1. additionwere added to the mixture,and it
  2. stirringwas stirred at room temperature for two additional hours
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. customthe residue was partitioned between water and ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-34a5c57ca0a54dc5a198b3862b3ed6c5
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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