Hydrochloric Acid → (2-Chloro-6-methylquinolin-4-yl)acetic acid

HRID 540276Notes

Reaction equation

HRID 540276 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:23])[CH:8]=2)[N:3]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]([OH:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:23])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86691430Diethyl (2-chloro-6-methylquinolin-4-yl)propanedioate

Product 1

HCID 83647169(2-Chloro-6-methylquinolin-4-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of diethyl (2-chloro-6-methylquinolin-4-yl)propanedioate (100 mg, 0.30 mmol) in methanol (2 mL) was added an aqueous solution of sodium hydroxide (2 N, 2 mL) and the resulting mixture was stirred at room temperature overnight. The reaction was then acidified to pH 4 with an aqueous solution of hydrochloric acid (5 N), and extracted with ethyl acetate (10 mL×3). The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the desired product as a white solid. MS (ESI+) [(M+H)+] 236.

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6fe87eabe6ed4320ad5135d6426601d2
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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