Ethyl 5-Amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate → 5-Amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

HRID 620883Notes

Reaction equation

HRID 620883 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([O:20]CC)=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1>Cl>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([Cl:14])=[C:8]2[C:3]=1[C:4](=[O:23])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Participants

3

Reactant 1

HCID 15052639Ethyl 5-Amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 148965465-Amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic AcidYield 89.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 17.2 g (50.2 mmol) of ethyl 5-amino-8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate in 100 ml of 6 M hydrochloric acid was refluxed for three hours. The mixture was cooled to room temperature, and the solids were filtered, washed with water and ether, and dried to give 14.2 g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-e29d5cd089b54187923a66eabd2b78f1
Source dataset
uspto-grants-1989_04
Patent number
US04822801

Reaction notes

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