Thionyl Chloride → HCID 19018948, compound

HRID 1110064Notes

Reaction equation

HRID 1110064 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]([CH:13]([CH3:16])[CH2:14]O)[CH:7]=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:5]2=[O:22].S(Cl)([Cl:25])=O>C(Cl)(Cl)Cl>[Cl:25][CH2:14][CH:13]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([F:12])[CH:10]=2)[C:5](=[O:22])[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:7]1)[CH3:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19018950HCID 19018950, compound

Product 1

HCID 19018948HCID 19018948, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4.45 gm (14.3 mmol) of ethyl 6,7-difluoro-1,4-dihydro-1-(1-hydroxyprop-2-yl)-4-oxoquinoline-3-carboxylate and 5.10 gm (42.9 mmol) of thionyl chloride were dissolved into 130 ml of chloroform for reaction with heating under refluxing for 1 hour. After cooling, the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (chloroform:methanol=100:1), and recrystallized from ethanol to obtain 3.53 gm of colorless, needlelike crystals of ethyl 1-(1-chloroprop-2-yl)-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate:

Workup

  1. temperaturewith heating
  2. temperatureunder refluxing for 1 hour
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:1)
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-af619f0082be44279a7700ea1f801df7
Source dataset
uspto-grants-1994_06
Patent number
US05324735

Reaction notes

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