Hydrochloric Acid → HCID 58492404, compound

HRID 68166Notes

Reaction equation

HRID 68166 reaction equation
Cl.[F:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[C:9]2[C:4]=1[C:5](=[O:39])[C:6]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][O:32]C3CCCCO3)=[CH:25][CH:24]=1)=[CH:7][N:8]2[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:8]1[C:9]2[C:4](=[C:3]([F:2])[CH:12]=[CH:11][C:10]=2[O:13][CH2:14][CH2:15][CH3:16])[C:5](=[O:39])[C:6]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][OH:32])=[CH:25][CH:24]=2)=[CH:7]1)[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58492568HCID 58492568, compound

Product 1

HCID 58492404HCID 58492404, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2N hydrochloric acid (6.3 ml) was added to an ethanol solution (20 ml) of ethyl (5-fluoro-4-oxo-8-propoxy-3-{4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-4H-quinolin-1-yl)acetate (840 mg, 1.59 mmol) and stirred at 50° C. for 2 hours. The resulting mixture was cooled to room temperature and then concentrated under reduced pressure. Ethyl acetate and water were added to the residue, followed by separation. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=30:1→15:1). The purified product was concentrated under reduced pressure, giving a pale yellow oily substance of ethyl{5-fluoro-3-[4-(2-hydroxyethoxy)phenyl]-4-oxo-8-propoxy-4H-quinolin-1-yl}acetate (627 mg, yield: 89%).

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionEthyl acetate and water were added to the residue
  4. customfollowed by separation
  5. washThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified
  8. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-db463c7788804fef93219af78f994f67
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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