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Acetic Acid → 5-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 47896
Notes
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Reaction equation

HRID 47896 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([F: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.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]([F: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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 14127986Ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Conditions

Temperature
105 °C

Procedure

28.7 g of ethyl 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (0.088 mol), 160 ml of acetic acid, and a mixture of 100 ml of water and 18 ml of concentrated sulfuric acid were stirred at 100-110° C. for 40 minutes. The reacting mixture was cooled and filtered. The precipitate was recrystallized from chloroform-ethanol to give 25.6 g 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (Sparcarboxylic acid, 0.086 mol), mp. 293-295C., in 98.0% yield.

Workup

  1. temperatureThe reacting mixture was cooled
  2. filtrationfiltered
  3. customThe precipitate was recrystallized from chloroform-ethanol

Sources & evidence

ORD record
ord-e605837b5210448cbdf47cd295dc0ba9
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699992B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes