HCID 59002835, compound → HCID 59002994, compound

HRID 561110Notes

Reaction equation

HRID 561110 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N:18](C)[C:19](=O)C(F)(F)F)[C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:26])[C:6]([C:27]([O:29]C)=[O:28])=[CH:5]2)[CH2:3][CH2:2]1>CC(O)=O.Cl>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH:18][CH3:19])[C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:26])[C:6]([C:27]([OH:29])=[O:28])=[CH:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 59002835HCID 59002835, compound

Product 1

HCID 59002994HCID 59002994, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-(N-methyltrifluoroacetamido)-4-oxoquinoline-3-carboxylate (880 mg, 2.03 mmol) in AcOH (10 mL), 6M HCl (5 mL) was added. The mixture was stirred at 100° C. for 4 h. After cooling, the solvent was removed by evaporation. 50 mL water was added, and the resulting precipitate was collected by filtration, washed with water and dried to give 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-methylamino-4-oxoquinoline-3-carboxylic acid (605 mg, 92%) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by evaporation
  3. addition50 mL water was added
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-ff1a8decc3774c2a9a7fa3d11c158e22
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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