ChemicalBook--->CAS DataBase List--->178964-53-9

178964-53-9

178964-53-9 Structure

178964-53-9 Structure
IdentificationBack Directory
[Name]

Descarboxyl Levofloxacin
[CAS]

178964-53-9
[Synonyms]

Levofloxacin-6
Levofloacin Impurity 4
Levofloxacin Impurity F
Levofloxacin Impurity 3
Decarboxyl Levofloxacin
Levofloacin Impurity 28
Levofloxacin impurity 28
Descarboxyl Levofloxacin
Levofloxacin EP Impurity E
Levofloxacin BP Impurity E
(S)-Ofloxacin EP Impurity B
Descarboxyl Levofloxacin HCl
Levofloxacin Descarboxy IMpurity
Descarboxyl Levofloxacin IMpurity
Decarboxylated levofloxacin hydrochloride
Levofloxacin Impurity E(Descarboxyl Levofloxacin)
(S)-Ofloxacin EP Impurity B (Decarboxyl Levofloxacin)
Levofloxacin?EP Impurity E (Levofloxacin Descarboxy Impurity)
(S)-9-Fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2H-[1,4]oxazino[2,3,4-ij]quinolin-7(3H)-one
(S)-9-fluoro-3-methyl-10- (4-methylpiperazin-1-yl)-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one
(3S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazin-7-one
7H-Pyrido[1,2,3-de]-1,4-benzoxazin-7-one, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-, (3S)-
(-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine
(S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one hydrochloride
(S)-9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one(Decarboxyl Levofloxacin)
Levofloxacin impurity 10/Descarboxyl Levofloxacin/(S)-Ofloxacin EP Impurity B/(S)-9-fluoro-3-methyl-10- (4-methylpiperazin-1-yl)-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinolin-7-one
[Molecular Formula]

C17H20FN3O2
[MDL Number]

MFCD28016445
[MOL File]

178964-53-9.mol
[Molecular Weight]

317.358
Questions And AnswerBack Directory
[Synthesis]

Descarboxyl Levofloxacin was prepared as follows:

Synthesis of 178964-53-9

Take 0.03 mol of levofloxacin (10.83 g) and place it in a pressure-resistant reaction flask equipped with a spherical condenser. Add 1000 ml of 1 mol/L hydrochloric acid solution and stir to dissolve at 60–80 °C. Heat at 120 °C and 0.3 MPa for 50 hours. Evaporate the solution to dryness in a 100 °C water bath while simultaneously allowing HCl to evaporate completely, yielding a residue of 9.45 g. Recrystallize the residue repeatedly using a mixed solvent of ethanol and acetone in a volume ratio of 2:1. The recrystallization includes the following steps:

(1) Crystallization: Add 100 times the weight of the mixed solvent to the residue, heat to 80°C, stir to dissolve the residue, filter, concentrate the filtrate to 2/3 volume, place in a 4°C refrigerator for 2 hours to precipitate crystals, filter, wash the crystals several times with the mixed solvent, combine the filtrate and washings, concentrate to 200 ml, place in a 4°C refrigerator for 2 hours to precipitate crystals, repeat the filtration, washing, and crystallization steps 3 times, combine the obtained crystals to obtain crude Descarboxyl Levofloxacin 1;

(2) Recrystallization: Take crude Descarboxyl Levofloxacin, add 150 times its weight of mixed solvent, heat to 60℃ and stir to dissolve the decarboxylated crude levofloxacin, filter, concentrate the filtrate to 2/5, place in a 4℃ refrigerator for 2 hours, crystals precipitate, filter, wash the crystals several times with mixed solvent, combine the filtrate and washings, concentrate to 200ml, place in a 4℃ refrigerator for 2 hours, crystals precipitate, repeat the filtration, washing and crystallization steps 3 times, combine the obtained crystals to obtain crude Descarboxyl Levofloxacin 2;

(3) Repeat step (2) 1-2 times, the obtained crystals are 8.3g, which is Descarboxyl Levofloxacin, with a yield of 87%.

Chemical PropertiesBack Directory
[Melting point ]

154-158°C
[Boiling point ]

501.1±50.0 °C(Predicted)
[density ]

1.35±0.1 g/cm3(Predicted)
[storage temp. ]

Refrigerator
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

7.37±0.42(Predicted)
[color ]

Off-White to Light Yellow
[InChI]

InChI=1S/C17H20FN3O2/c1-11-10-23-17-15-12(14(22)3-4-21(11)15)9-13(18)16(17)20-7-5-19(2)6-8-20/h3-4,9,11H,5-8,10H2,1-2H3/t11-/m0/s1
[InChIKey]

XTLCAWXSWVQNHK-NSHDSACASA-N
[SMILES]

O1C2=C(N3CCN(C)CC3)C(F)=CC3C(=O)C=CN(C2=3)[C@@H](C)C1
[CAS DataBase Reference]

178964-53-9
Hazard InformationBack Directory
[Chemical Properties]

Off-White to Pale Yellow Solid
[Uses]

A degradation product of Levofloxacin (L360000).
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