Ethyl 1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylate → HCID 15023844, compound

HRID 1648645Notes

Reaction equation

HRID 1648645 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:20]([O-])=O)[C:10]([F:19])=[C:11]([F:18])[C:12]=3[O:14][CH:15]([F:17])[F:16])[C:7](=[O:23])[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5]2)[CH2:3][CH2:2]1.[H][H]>C(O)(=O)C.[Pd]>[NH2:20][C:9]1[C:10]([F:19])=[C:11]([F:18])[C:12]([O:14][CH:15]([F:16])[F:17])=[C:13]2[C:8]=1[C:7](=[O:23])[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5][N:4]2[CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 15023843Ethyl 1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 15023844HCID 15023844, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

3.0 g (0.0074 moles) of ethyl 1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylate [(XX), R1 =--OCHF2, R3' =NO2, R17 =C2H5, X=F] [prepared as described in step (e) above] were dissolved in 800 ml of acetic acid by heating. 0.75 g of 5% w/w palladium-on-carbon was then added to the solution, and the mixture was stirred at 70°-80° C. for 3 hours under a current of hydrogen. At the end of this time, the reaction mixture was filtered, and the filtrate was concentrated by evaporation under reduced pressure. The residue was washed with diethyl ether to give 1.78 g of ethyl 5-amino-1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate as a colorless powder, melting at 295°-296° C.

Workup

  1. temperatureby heating
  2. filtrationAt the end of this time, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-d13a3b435ed74cf8a23c94cce1f6b50a
Source dataset
uspto-grants-1995_07
Patent number
US05436367

Reaction notes

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