Acetic Acid → 8-Bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1761654Notes

Reaction equation

HRID 1761654 reaction equation
[Br:1][C:2]1[C:3]([F:22])=[C:4]([F:21])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([O:17]CC)=[O:16])[C:7]2=[O:20].C(O)(=O)C.S(=O)(=O)(O)O>O>[Br:1][C:2]1[C:3]([F:22])=[C:4]([F:21])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([OH:17])=[O:16])[C:7]2=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 11046932Ethyl 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 137488068-Bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 88.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 8-bromo-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (1.0 g), acetic acid (4 ml), water (3 ml) and concentrated sulfuric acid (0.5 ml) was heated on an oil bath (90°-100° C.) for an hour under stirring, then for an hour at room temperature and poured into ice water (20 ml). The resulting precipitate was collected by filtration and washed with water to give the title compound (0.82 g), mp 224°-225.5° C.

Workup

  1. temperaturewas heated on an oil bath (90°-100° C.) for an hour
  2. waitfor an hour at room temperature
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-77311101f02b4f1b8c78a2f83b976ca4
Source dataset
uspto-grants-1989_05
Patent number
US04826982

Reaction notes

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