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Sodium Hydroxide → (6-Methylpyridin-3-yl)acetic acid

HRID 1402748
Notes
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Reaction equation

HRID 1402748 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70218796HCID 70218796, compound

Product 1

HCID 22507698(6-Methylpyridin-3-yl)acetic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of methyl (6-methylpyridin-3-yl)acetate (60 mg, 0.36 mmol) in methanol (5 ml) was added NaOH (1.0 ml of a 2M aqueous solution, 2.0 mmol) and the resulting solution was heated at 65° C. for 2 hours. The solvent was then removed at reduced pressure and the resulting residue was dissolved in methanolic HCl (5 ml) and then reconcentrated to yield the title product (54 mg, quant. yield) that was used without further purification.

Workup

  1. customThe solvent was then removed at reduced pressure
  2. dissolutionthe resulting residue was dissolved in methanolic HCl (5 ml)

Sources & evidence

ORD record
ord-c3ba509f4e4840ceab22ea9d201ac51e
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08912176B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes