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

HRID 561140Notes

Reaction equation

HRID 561140 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:22])[C:5]([C:17]([O:19]CC)=[O:18])=[CH:6][N:7]2[CH3:16].[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:22])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59003029Ethyl 5-amino-1-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate

Product 1

HCID 590028475-Amino-1-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acidYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-amino-1-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (203 mg, 0.650 mmol) and 1M aq. NaOH (2 mL) in EtOH (5 mL) was stirred at 50° C. for 1 h. The solvent was removed and the residue was dissolved in water. The solution was acidified to pH 7 with 2M HCl and the resulting precipitate was removed by filtration, washed with water, and dried to yield 5-amino-1-methyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (180 mg, 97%) as a pale yellow solid.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in water
  3. customthe resulting precipitate was removed by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-be6768affbee4e6cb39b6ce7802d7a83
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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