Hydrochloric Acid → 8-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 622584

Reaction equation

HRID 622584 reaction equation
[Cl: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].Cl>O1CCCC1>[Cl: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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13579166Ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 98359418-Chloro-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 75.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 1.1 g (3.36 mmol) of ethyl 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 10 ml of 6N hydrochloric acid, and 1 ml of tetrahydrofuran was refluxed for 21/2 hours. The mixture was cooled to room temperature, and the solids were filtered, washed with water and ether, and dried to give 0.76 g of the title compound as a white powder, m.p. 189°-191° C.

Workup

  1. temperaturewas refluxed for 21/2 hours
  2. filtrationthe solids were filtered
  3. washwashed with water and ether
  4. customdried

Sources & evidence

ORD record
ord-9dbc1857baba4be7b8d1f40413f8dd42
Source dataset
uspto-grants-1988_09
Patent number
US04771054

Linked notes

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