Hydrochloric Acid → HCID 59002961, compound

HRID 561166Notes

Reaction equation

HRID 561166 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:21]([O:23]CC)=[O:22])=[CH:6][N:7]2[CH:18]1[CH2:20][CH2:19]1.[OH-].[Na+].Cl>CCO>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH:15]([CH3:17])[CH3:16])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:21]([OH:23])=[O:22])=[CH:6][N:7]2[CH:18]1[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59002866HCID 59002866, compound

Product 1

HCID 59002961HCID 59002961, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-isopropoxy-4-oxoquinoline-3-carboxylate (125 mg, 0.341 mmol) and 1M aq. NaOH (0.5 mL) in EtOH (1.5 mL) was stirred at 50° C. for 1 h. After 2M HCl was added to the reaction mixture to pH<3, the crude product was extracted with EtOAc, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The residue was dried in vacuo to yield 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-isopropoxy-4-oxoquinoline-3-carboxylic acid (113 mg, 98%) as a yellow solid.

Workup

  1. extractionthe crude product was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-b045fdbef10241b5b51298429e46cc62
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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