Sodium Hydroxide → 5-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-2-methyl-4-oxoquinoline-3-carboxylic acid

HRID 561149Notes

Reaction equation

HRID 561149 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:25])[C:5]([C:20]([O:22]CC)=[O:21])=[C:6]([CH3:19])[N:7]2[CH:16]1[CH2:18][CH2:17]1.[OH-].[Na+]>CCO>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:25])[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH3:19])[N:7]2[CH:16]1[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66999763Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-2-methyl-4-oxoquinoline-3-carboxylate

Product 1

HCID 590029525-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-2-methyl-4-oxoquinoline-3-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-2-methyl-4-oxoquinoline-3-carboxylate (187 mg, 0.531 mmol) and 1M aq. NaOH (1 mL) in EtOH (3 mL) was stirred at 50° C. for 1 h. After the reaction mixture was concentrated in vacuo, the residue was dissolved in water and 2M HCl was added to pH<3. The resulting precipitate was collected by filtration in vacuo, washed with water and dried to yield 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-2-methyl-4-oxoquinoline-3-carboxylic acid (161 mg, 93%) as a pale yellow solid.

Workup

  1. concentrationAfter the reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water
  3. addition2M HCl was added to pH<3
  4. filtrationThe resulting precipitate was collected by filtration in vacuo
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-16c805cd760c4851ab117a48de51bd5f
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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