Hydrochloric Acid → 3-Aminopicolinic acid

HRID 2111865

Reaction equation

HRID 2111865 reaction equation
[N+:1]([C:4]1[C:5]([C:10]([OH:12])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.C(=O)([O-])O.[Na+].[H][H].Cl>O.[Pd]>[NH2:1][C:4]1[C:5]([C:10]([OH:12])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Procedure

3-nitropyridine-2-carboxylic acid (2.72 g, 16.2 mmol) and sodium hydrogencarbonate (1.34 g, 16.2 mmol) were dissolved in distilled water (20 mL), and the atmosphere in the system was replaced by nitrogen. After adding 10% palladium charcoal (1.72 g), the atmosphere in the system was replaced by hydrogen, and the mixture stirred at room temperature for 50 hours. 1N hydrochloric acid aqueous solution was added, and the pH of the reaction solution was adjusted to weak acidity. The solvent was distilled off under reduced pressure, a small amount of ethanol and ethyl acetate were added to the residue, and the precipitate produced was filtered off. The filtrate was concentrated, and the target substance (1.50 g, 67%) was thus obtained as a light yellow solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additiona small amount of ethanol and ethyl acetate were added to the residue
  3. customthe precipitate produced
  4. filtrationwas filtered off
  5. concentrationThe filtrate was concentrated
  6. customthe target substance (1.50 g, 67%) was thus obtained as a light yellow solid

Sources & evidence

ORD record
ord-ca25a76da2be49cb90ffdf6819e6a541
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Linked notes

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