Lithium hydroxide, monohydrate → 2-(3,4,5-Trimethoxyphenylethynyl)pyridine-4-carboxylic Acid

HRID 1634899Notes

Reaction equation

HRID 1634899 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[CH:18]=[CH:17][N:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].O.[OH-].[Li+]>CO>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][N:16]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 18674974Ethyl 2-(3,4,5-trimethoxyphenylethynyl)pyridine-4-carboxylate

Product 1

HCID 186750082-(3,4,5-Trimethoxyphenylethynyl)pyridine-4-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(3,4,5-trimethoxyphenylethynyl)pyridine-4-carboxylate (1.40 g) was suspended in methanol (100 mL), to the suspension lithium hydroxide hydrate (189 mg) was added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue and the resultant mixture was neutralized with 1 M hydrochloric acid. After the reaction mixture was cooled with ice, crystals precipitated were collected by filtration to obtain the title compound as colorless crystals.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. temperatureAfter the reaction mixture was cooled with ice, crystals
  5. customprecipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-91c4c7b83f194cd29e276cd14a143adc
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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