Acetic Acid → 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-Carboxylic Acid

HRID 600908Notes

Reaction equation

HRID 600908 reaction equation
[F:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([O:19]CC)=[O:18])=[CH:8][N:9]2[C@@H:13]2[CH2:15][C@@H:14]2[F:16])=[C:4]([OH:23])[CH:3]=1.C(O)(=O)C.Cl>O>[F:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][N:9]2[C@@H:13]2[CH2:15][C@@H:14]2[F:16])=[C:4]([OH:23])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 67271258ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 672715427-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-Carboxylic AcidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-5-hydroxy-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (325 mg, 1.005 mmol), acetic acid (3 ml) and concentrated hydrochloric acid (1.5 ml) was heated under reflux for 2 hours in an oil bath at 120° C. After then adding water (30 ml) and cooling with ice, the crystals formed were filtered out and then washed with water, 5% aqueous ethanol solution, and diethyl ether to obtain 267 mg (90%) of the title compound as a pale-yellow powder.

Workup

  1. temperaturewas heated
  2. customthe crystals formed
  3. filtrationwere filtered out
  4. washwashed with water, 5% aqueous ethanol solution, and diethyl ether

Sources & evidence

ORD record
ord-eba78f3f52794950b5c3f1bdf283bb27
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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