HCID 14096377, compound → 5-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 2249251Notes

Reaction equation

HRID 2249251 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:18]([O-])=O)[C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1>C(O)C.CN(C=O)C.[H][H].[C].[Pd]>[NH2:18][C:9]1[C:10]([F:17])=[C:11]([F:16])[C:12]([O:14][CH3:15])=[C:13]2[C:8]=1[C:7](=[O:21])[C:6]([C:22]([OH:24])=[O:23])=[CH:5][N:4]2[CH:1]1[CH2:2][CH2:3]1

Participants

5

Reactant 1

HCID 14096377HCID 14096377, compound

Product 1

HCID 105668945-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 62.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 19794673N,N-dimethylformamide ethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a solution of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxo-3-quinolinecarboxylic acid (322 mg) in ethanol-DMF (4:1) was added 10% palladium-carbon (25 mg) and the mixture was stirred in hydrogen gas atomosphere for 6 hours at room temperature. The catalyst was filtered off and washed with a solution of chloroform-methanol-concentrated aqueous ammonia (10:10:3) The filtrate and washings were combined and concentrated. The residue was recrystallized from a solution of chloroform-methanol-concentrated aqueous ammonia (20:6:1) to give the title compound (183 mg) as yellow prisms, mp 291°-291.5° C. (decompd.).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with a solution of chloroform-methanol-concentrated aqueous ammonia (10:10:3) The filtrate and washings
  3. concentrationconcentrated
  4. customThe residue was recrystallized from a solution of chloroform-methanol-concentrated aqueous ammonia (20:6:1)

Sources & evidence

ORD record
ord-6f53b53867b34b349a951703b1513813
Source dataset
uspto-grants-1991_08
Patent number
US05043450

Reaction notes

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