Pyridine → HCID 621233, compound

HRID 1578279Notes

Reaction equation

HRID 1578279 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][N:9]2[CH2:12][CH2:13]O)=[CH:4][C:3]=1[F:21].N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].S(Cl)([Cl:36])=O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][N:9]2[CH2:12][CH2:13][Cl:36])=[CH:4][C:3]=1[F:21]

Participants

5

Reactant 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 6178607-Chloro-6-fluoro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, ethyl ester

Product 1

HCID 621233HCID 621233, compoundYield 80%

Procedure

27 g of the foregoing ester product were added, portionwise, to an agitated and cooled solution of pyridine (8.1 cm3) in thionyl chloride (54 cm3). The addition was carried out at such a rate that the temperature of the mixture remained between 0° and 5° C. After returning to room temperature, the solution was heated for 1 hour under reflux and the excess of reagent was then removed by distillation under reduced pressure. The residue was added, with agitation, to 100 cm3 of iced water. The suspension obtained was neutralised by the addition of 10% aqueous Na2CO3. The precipitate obtained was filtered off, washed with water and recrystallised from ethanol (480 cm3). 22.4 g of 7-chloro-1-(2-chloroethyl)-3-ethoxycarbonyl-6-fluoro-4-oxo-1,4-dihydro-quinoline, m.p. 222° C., were obtained; yield 80%.

Workup

  1. additionThe addition
  2. customremained between 0° and 5° C
  3. customAfter returning to room temperature
  4. temperaturethe solution was heated for 1 hour
  5. temperatureunder reflux
  6. customthe excess of reagent was then removed by distillation under reduced pressure
  7. additionThe residue was added, with agitation, to 100 cm3 of iced water
  8. customThe suspension obtained
  9. customThe precipitate obtained
  10. filtrationwas filtered off
  11. washwashed with water
  12. customrecrystallised from ethanol (480 cm3)

Sources & evidence

ORD record
ord-9a9ba1ca650e4991835d4b9a579c1720
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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