Hydrochloric Acid → 3-Acetylpyridine-2-carboxylic acid

HRID 2372189Notes

Reaction equation

HRID 2372189 reaction equation
[C:1]([C:4]1[C:5]([C:10]([O:12]C)=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].O.[OH-].[Li+].Cl>C(O)C.O>[C:1]([C:4]1[C:5]([C:10]([OH:12])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 15257078Methyl 3-acetyl-2-pyridinecarboxylate

Product 1

HCID 230026683-Acetylpyridine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To methyl 3-acetyl-2-pyridinecarboxylate (1.86 g) in 20 ml of ethanol is added lithium hydroxide monohydrate (10 mmol) in 20 ml of hot water. After 1 hour, conc. hydrochloric acid (1 ml) is added, and the mixture is reduced under vacuum. The resulting solid is extracted with hot methylene chloride, and the residue is stirred with 15 ml of THF for 1 hour at 60°, then filtered and dried to give 3-acetyl-2-pyridinecarboxylic acid.

Workup

  1. extractionThe resulting solid is extracted with hot methylene chloride
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-aa241aa4413240a897f3a72991b7d453
Source dataset
uspto-grants-1992_03
Patent number
US05098462

Reaction notes

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