Thionyl Chloride → HCID 14989579, compound

HRID 1110061Notes

Reaction equation

HRID 1110061 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:13])[C:11]=1[F:12])[N:8]([CH:14]([CH3:17])[CH2:15]O)[CH:7]=[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:5]2=[O:23].S(Cl)([Cl:26])=O>C(Cl)(Cl)Cl>[Cl:26][CH2:15][CH:14]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([F:12])[C:10]=2[F:13])[C:5](=[O:23])[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:7]1)[CH3:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5084511HCID 5084511, compound

Product 1

HCID 14989579HCID 14989579, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.988 gm (3.0 mmol) of ethyl 6,7,8-trifluoro-1,4-dihydro-1-(1-hydroxyprop-2-yl)-4-oxoquinoline-3-carboxylate was dissolved into 50 ml of chloroform. To this was added 0.714 gm (6.0 mmol) of thionyl chloride and the mixture was reacted with heating under refluxing for 10 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain 1.001 gm of colorless, needlelike crystals of ethyl 1-(1-chloroprop-2-yl)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Workup

  1. customthe mixture was reacted
  2. temperaturewith heating
  3. temperatureunder refluxing for 10 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-84a8bf21025a41fa909cb56624279eb8
Source dataset
uspto-grants-1994_06
Patent number
US05324735

Reaction notes

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