Hydrochloric Acid → HCID 58492404, compound

HRID 2048004Notes

Reaction equation

HRID 2048004 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:39])[CH2:6][N:7]1[C:16]2[C:11](=[C:12]([F:21])[CH:13]=[CH:14][C:15]=2[O:17][CH2:18][CH2:19][CH3:20])[C:10](=[O:22])[C:9]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][O:32]C3CCCCO3)=[CH:25][CH:24]=2)=[CH:8]1)[CH3:3]>C(O)C>[F:21][C:12]1[CH:13]=[CH:14][C:15]([O:17][CH2:18][CH2:19][CH3:20])=[C:16]2[C:11]=1[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][OH:32])=[CH:25][CH:24]=1)=[CH:8][N:7]2[CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:39]

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-072cc9c4b00847af96280fa9f14baacb
Source dataset
uspto-grants-2013_11
Patent number
US08592593B2

Reaction notes

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