Water → 5-Nitropicolinic acid

HRID 374417Notes

Reaction equation

HRID 374417 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10](C(OCC)=O)C(OCC)=O)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH-:21].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:29]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:29])=[O:21])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 516875Potassium Permanganate2×HCID 2794558Diethyl 2-(5-nitropyridin-2-yl)malonate

Product 1

HCID 5204885-Nitropicolinic acid

Conditions

Temperature
60 °C

Procedure

Diethyl 2-(5-nitropyridin-2-yl)malonate (67.47 g) was stirred in water and aqueous sodium hydroxide solution (2N) was added followed by potassium permanganate (42 g) causing the reaction temperature to rise to 60° C. Further portions of aqueous sodium hydroxide solution and potassium permanganate were added maintaining the reaction temperature at 60°-70° C. After the final addition, the suspension was stirred at 60° C. for 1.5 hours. The hot suspension was then filtered through `Hyflo Supercel`. The filter cake was washed with aqueous sodium hydroxide solution (2N). On cooling to room temperature, the filtrate was carefully acidified to pH 1-2 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration and dried to yield 5-nitropyridine-2-carboxylic acid (26.17 g) as a fawn solid, m.p. 210°-211° C.

Workup

  1. customto rise to 60° C
  2. temperaturemaintaining the reaction temperature at 60°-70° C
  3. additionAfter the final addition
  4. filtrationThe hot suspension was then filtered through `Hyflo Supercel`
  5. washThe filter cake was washed with aqueous sodium hydroxide solution (2N)
  6. temperatureOn cooling to room temperature
  7. filtrationThe resulting precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-d30c23b8206947fb9e3bfde8907309fa
Source dataset
uspto-grants-1996_01
Patent number
US05480857

Reaction notes

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