Hydrochloric Acid → HCID 178477333, compound

HRID 2405826Notes

Reaction equation

HRID 2405826 reaction equation
C([O:3][C:4]([C:6]1[C:7]([S:18][CH2:19][CH3:20])=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:17])=[O:5])C.[OH-].[Na+].Cl>C1COCC1.CO>[Cl:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[N:8]=[C:7]([S:18][CH2:19][CH3:20])[C:6]([C:4]([OH:5])=[O:3])=[C:15]2[OH:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178470104HCID 178470104, compound

Product 1

HCID 178477333HCID 178477333, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 8-chloro-2-ethylsulfanyl-4-hydroxy-quinoline-3-carboxylic acid ethyl ester (19.81 g, 63.5 mmol) in THF:MeOH (1:1, 150 mL) at room temperature was added 1N NaOH. The reaction was allowed to stir at reflux for 24 hours, monitoring by HPLC. Upon the completion of the reaction, the mixture was acidified with 4N HCl and extracted 3 times with dichloromethane. The organic phases were combined, dried over Mg2SO4, and concentrated in vacuo to afford 8-chloro-2-ethylsulfanyl-4-hydroxy-quinoline-3-carboxylic acid (17.17 g, 95% yield). LCMS found 383.88 [M+H]+.

Workup

  1. temperatureat reflux for 24 hours
  2. customUpon the completion of the reaction
  3. extractionextracted 3 times with dichloromethane
  4. dry with materialdried over Mg2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b41f01f2f61455dbc44efff305b906a
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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