Hydrochloric Acid → 5-Amino-1-cyclopropyl-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1078269Notes

Reaction equation

HRID 1078269 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([CH3:14])=[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>C(O)(=O)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([F:13])[C:9]([CH3:14])=[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[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10519846Ethyl 5-amino-1-cyclopropyl-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 108513065-Amino-1-cyclopropyl-6,7-difluoro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 14.8 g of ethyl 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylate, 37.2 ml of hydrochloric acid and 150 ml of 90% acetic acid was heated at reflux for 2 hours. After cooling, the deposited crystals were collected by filtration and washed with water to give 11.8 g of the desired compound as yellow crystals. The crystals were subsequently recrystallized from N,N-dimethylformamide to give yellow crystals, m.p. 290.5° C. (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationthe deposited crystals were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-bf7126cbe977486cb976473a13ab3c01
Source dataset
uspto-grants-1996_08
Patent number
US05547962

Reaction notes

Loading…