Acetic Acid → 5-Amino-1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1440106Notes

Reaction equation

HRID 1440106 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH:15]([F:17])[F:16])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:21]([O:23]CC)=[O:22])=[CH:6][N:7]2[CH:18]1[CH2:20][CH2:19]1.C(O)(=O)C.S(=O)(=O)(O)O>O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([O:14][CH:15]([F:16])[F:17])=[C:8]2[C:3]=1[C:4](=[O:26])[C:5]([C:21]([OH:23])=[O:22])=[CH:6][N:7]2[CH:18]1[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 15023844HCID 15023844, compound

Product 1

HCID 150238455-Amino-1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 3.58 g (0.0096 moles) of ethyl 5-amino-1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate [(XXII), R1 =--OCHF2, R17 =C2H5, X=F] [prepared as described in step (f) or (f') above], 21 ml of acetic acid, 2.8 ml of concentrated sulfuric acid and 15 ml of water was heated under reflux, with stirring, for 1 hour, after which it was cooled by allowing it to stand. Water was then added to the reaction mixture, and the insoluble materials were removed by filtration and washed with water and with diethyl ether, in that order, to give 3.0 g of 5-amino-1-cyclopropyl-8-difluoromethoxy-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as a pale yellowish green powder, melting at 284°-286° C.

Workup

  1. customprepared
  2. temperatureunder reflux
  3. temperatureafter which it was cooled
  4. customthe insoluble materials were removed by filtration
  5. washwashed with water and with diethyl ether, in that order

Sources & evidence

ORD record
ord-86b35d4723224598ba26cfdce3f38064
Source dataset
uspto-grants-1996_03
Patent number
US05496951

Reaction notes

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