Tetrahydrofuran → HCID 58492478, compound

HRID 1474563Notes

Reaction equation

HRID 1474563 reaction equation
C1COCC1.C([O:13][C:14]1[CH:47]=[CH:46][C:17]([C:18]([O:20][CH2:21][N:22]2[C:31]3[C:26](=[C:27]([F:36])[CH:28]=[CH:29][C:30]=3[O:32][CH2:33][CH2:34][CH3:35])[C:25](=[O:37])[C:24]([C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)=[CH:23]2)=[O:19])=[CH:16][CH:15]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][N:22]2[C:31]3[C:26](=[C:27]([F:36])[CH:28]=[CH:29][C:30]=3[O:32][CH2:33][CH2:34][CH3:35])[C:25](=[O:37])[C:24]([C:38]3[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=3)=[CH:23]2)=[O:19])=[CH:46][CH:47]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 58492555HCID 58492555, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58492478HCID 58492478, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium/carbon (260 mg) was added to a THF (30 ml) and ethanol (15 ml) solution of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-ylmethyl 4-benzyloxybenzoate (2.6 g, 4.6 mmol). The mixture was subjected to hydrogen substitution and stirred at room temperature for 3 hours. After completion of the reaction, the catalyst was removed by conducting filtration using Celite, and the mixture was concentrated to dryness under reduced pressure, giving a pale yellow powder of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-ylmethyl 4-hydroxybenzoate (2.22 g, yield: quantitative).

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed
  3. filtrationfiltration
  4. concentrationthe mixture was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-95088d6d08094a01b4c4a9c7950af86f
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

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