Flumequine → HCID 21445337, compound

HRID 1287881Notes

Reaction equation

HRID 1287881 reaction equation
[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16](O)=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[CH:3]=1.S(Cl)([Cl:22])=O>>[F:1][C:2]1[CH:14]=[C:12]2[C:13]3[N:8]([CH:9]=[C:10]([C:16]([Cl:22])=[O:17])[C:11]2=[O:15])[CH:7]([CH3:19])[CH2:6][CH2:5][C:4]=3[CH:3]=1

Participants

3

Reactant 2

HCID 3374FlumequineHCID 24386Thionyl Chloride

Product 1

HCID 21445337HCID 21445337, compound

Procedure

6,7Dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid (5.0 g., 0.0192 mole) is stirred with thionyl chloride (75 ml.), and the mixture is heated to its reflux temperature and maintained at reflux for about 18 hours. The mixture is evaporated to dryness, then azeotroped thrice with 50 ml. portions of benzene to provide an off-white solid, 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H-benzo[ij]quinolizine-2-carboxylic chloride, m.p. 183°-186° C.

Workup

  1. temperaturethe mixture is heated to its
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for about 18 hours
  5. customThe mixture is evaporated to dryness
  6. customazeotroped thrice with 50 ml

Sources & evidence

ORD record
ord-fb59a2ef9ea444809a262921b5d0e5d7
Source dataset
uspto-grants-1976_10
Patent number
US03985882

Reaction notes

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