Hydrochloric Acid → 2-Aminonicotinic acid

HRID 2035765Notes

Reaction equation

HRID 2035765 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>C1COCC1>[NH2:1][C:2]1[C:3]([C:4]([OH:6])=[O:5])=[CH:8][CH:9]=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 351633Methyl 2-aminopyridine-3-carboxylate

Product 1

HCID 729302-Aminonicotinic acidYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-aminonicotinate (4 g) and 2M aqueous sodium hydroxide solution (35 mL) in THF (50 ml) was stirred at room temperature overnight. The reaction mixture was neutralized with 1M hydrochloric acid, and extracted with ethyl acetate. The aqueous layer was acidified with 1M hydrochloric acid, and extracted with THF. The organic layers were combined, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (1.78 g) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with THF
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8fed00f3106041349e3eb89d0bac334b
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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