Hydrochloric Acid → HCID 59002917, compound

HRID 561158Notes

Reaction equation

HRID 561158 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([O:21]CC)=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.[OH-].[Na+].Cl>CCO>[NH2:1][C:2]1[C:11]([Cl:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59002870HCID 59002870, compound

Product 1

HCID 59002917HCID 59002917, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 5-amino-6-chloro-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (236 mg, 0.665 mmol) and 1M aq. NaOH (1.06 mL, 1.06 mmol) in EtOH (3 mL) was stirred at 50° C. for 1 h. To the reaction mixture, ice-water and 2M HCl was added to pH<3 and the resulting precipitate was collected by filtration in vacuo, washed with water and dried to yield 5-amino-6-chloro-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (204 mg, 94%) as a pale yellow solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration in vacuo
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-fb8e62d3e7f0494dab96f89998636753
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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