Acetic Acid → HCID 67271655, compound

HRID 600906Notes

Reaction equation

HRID 600906 reaction equation
[Cl:1][C:2]1[C:11]([Cl: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])=[CH:4][CH:3]=1.C(O)(=O)C.Cl>O>[Cl:1][C:2]1[C:11]([Cl: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])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 67270783HCID 67270783, compound

Product 1

HCID 67271655HCID 67271655, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of ethyl 7,8-dichloro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.114 g, 3.237 mmol), acetic acid (8 ml) and concentrated hydrochloric acid (4 ml) was heated under reflux for 2 hours in an oil bath at 130° C. After then adding water (40 ml) and cooling with ice, the crystals formed were filtered out and washed with water (5 ml×2), 5% aqueous ethanol solution (5 ml×2), and diethyl ether (5 ml×2), thereby obtaining 909 mg (89%) 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 ml×2), 5% aqueous ethanol solution (5 ml×2), and diethyl ether (5 ml×2)

Sources & evidence

ORD record
ord-1b1b1316e0db48cba526b5eef66fe0fe
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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