Hydrochloric Acid → 2-Aminonicotinic acid

HRID 1747879Notes

Reaction equation

HRID 1747879 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-b75c3e14032741eea3a96638f81c6b38
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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