Lithium Hydroxide → HCID 15166992, compound

HRID 1494304Notes

Reaction equation

HRID 1494304 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][S:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]([O:20]C)=[O:19])[CH:9]=1)=[O:4].[Li+].[OH-]>CO>[C:3]([CH2:5][CH2:6][S:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]([OH:20])=[O:19])[CH:9]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15166991HCID 15166991, compound

Product 1

HCID 15166992HCID 15166992, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This methyl 4-(2-methoxycarbonylethylthio)quinoline-2-carboxylate is hydrolyzed by the addition of 3 equivalents of aqueous lM LiOH in MeOH/H20 and stirring at RT. After stirring for 16 hours, the methanol is evaporated, the residue diluted with water and extracted 2x with ethyl acetate. The aqueous layer is acidified to pH 1.5 by the addition of aqueous lN HCl and the solid obtained is filtered, washed with water, and dried to afford 4-(2-carboxyethylthio)quinoline-2-carboxylic acid.

Workup

  1. stirringAfter stirring for 16 hours
  2. customthe methanol is evaporated
  3. additionthe residue diluted with water
  4. extractionextracted 2x with ethyl acetate
  5. additionThe aqueous layer is acidified to pH 1.5 by the addition of aqueous lN HCl
  6. customthe solid obtained
  7. filtrationis filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-4ab9eb00498c4410a1d7ce21e6ed1be0
Source dataset
uspto-grants-1991_06
Patent number
US05026700

Reaction notes

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