Water → HCID 178470130, compound

HRID 893573Notes

Reaction equation

HRID 893573 reaction equation
[Cl:1][C:2]1[C:3]([F:23])=[C:4]([F:22])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([S:12]COC)[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]2[OH:21].O>O1CCOCC1.Cl>[Cl:1][C:2]1[C:3]([F:23])=[C:4]([F:22])[CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([SH:12])[C:8]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]2[OH:21]

Participants

5

Reactant 2

HCID 962WaterHCID 178470111HCID 178470111, compound

Product 1

HCID 178470130HCID 178470130, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 15.7 g of ethyl 8-chloro-6,7-difluoro-4-hydroxy-2-(methoxymethylthio)quinoline-3-carboxylate in 125 ml of 1,4-dioxane, 95 ml of 35% hydrochloric acid was added dropwise at 40° C. with stirring. The mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into 500 ml of water. The precipitate was collected by filtration and recrystallized from acetonitrile to give 11.2 g of the desired compound as pale yellow needles, m.p. 125°-130° C. (decomp.).

Workup

  1. stirringThe mixture was stirred at the same temperature for 1 hour
  2. filtrationThe precipitate was collected by filtration
  3. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-5e0a652d599a4febb0aa061571e1ce24
Source dataset
uspto-grants-1992_06
Patent number
US05126337

Reaction notes

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