Hydrochloric Acid → 5-Acetylpyridine-3-carboxylic acid

HRID 1048958Notes

Reaction equation

HRID 1048958 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]([O:12]C)=[O:11])[CH:7]=[N:8][CH:9]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([C:4]1[CH:5]=[C:6]([C:10]([OH:12])=[O:11])[CH:7]=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 596459Methyl 5-acetylpyridine-3-carboxylate

Product 1

HCID 218549245-Acetylpyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-acetylpyridine-3-carboxylate (0.15 g, 0.84 mmol) in methanol (2.10 mL) was added aqueous 1N sodium hydroxide solution (2.51 mL, 2.51 mmol). The resulting mixture was stirred at room temperature for 1 hour, then concentrated under reduced pressure to give a residue that was acidified with aqueous 1 N hydrogen chloride solution and extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered and concentrated to provide the title compound: 1H NMR (500 MHz, CDCl3) δ 9.43 (d, J=1.4 Hz, 1 H), 9.36 (s, 1 H), 8.84 (s, 1 H), 2.70 (s, 3 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a residue that
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-735881d496a942f4aed5f32650af7eae
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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