Water → 6-[(2-Aminoethyl)amino]-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 898110Notes

Reaction equation

HRID 898110 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1F.[CH2:20]([NH2:23])[CH2:21][NH2:22].O>CN(C)C(=O)C>[NH2:22][CH2:21][CH2:20][NH:23][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[Cl:1])[N:9]([CH:12]1[CH2:14][CH2:13]1)[CH:8]=[C:7]([C:15]([OH:17])=[O:16])[C:6]2=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 3301EthylenediamineHCID 483180Fluoroquinolonic acid

Product 1

HCID 179804946-[(2-Aminoethyl)amino]-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 10%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
115 °C

Procedure

7-Chloro-1-cyclopropyl-1,4-dihydro-6-fluoro4-oxo-quinoline-3-carboxylic acid (56.3 g) and ethylenediamine (36 g) were dissolved in N,N-dimethylacetamide (650 mL) at 100° C. and stirred for 8.5 h at 115° C. Water (700 mL) was added to the reaction mixture cooled at room temperature. The reaction mixture was stirred at room temperature for 2 h, cooled at 0-5° C. and stirred for 1 h. The precipitate obtained was filtered, washed with cold water, cold EtOH, and dried at 110° C. under reduced pressure for 1 h. The crude product was treated with HCl (6% aqueous solution) heating for 1 h in the presence of charcoal. After filtration, the solution was cooled to 35-40° C. and a first precipitation happened. The precipitate was filtered, washed with water and dried at 110° C. for 1 h. The title compound (6.4 g) was obtained as the hydrochloride salt. The hydrochloride salt was then converted to the free base using standard conditions.

Workup

  1. temperaturecooled at room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 2 h
  3. temperaturecooled at 0-5° C.
  4. stirringstirred for 1 h
  5. customThe precipitate obtained
  6. filtrationwas filtered
  7. washwashed with cold water, cold EtOH
  8. customdried at 110° C. under reduced pressure for 1 h
  9. additionThe crude product was treated with HCl (6% aqueous solution)
  10. temperatureheating for 1 h in the presence of charcoal
  11. filtrationAfter filtration
  12. temperaturethe solution was cooled to 35-40° C.
  13. customa first precipitation
  14. filtrationThe precipitate was filtered
  15. washwashed with water
  16. customdried at 110° C. for 1 h

Sources & evidence

ORD record
ord-ad37b714cf6b4a51939c308075b4d8e7
Source dataset
uspto-grants-2008_04
Patent number
US07351696B2

Reaction notes

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