Water → 6-methyl-4-nitropicolinic acid

HRID 552482Notes

Reaction equation

HRID 552482 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]#N)[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.N([O-])=[O:14].[Na+].[OH2:17]>S(=O)(=O)(O)O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:14])=[O:17])[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 113786726-Methyl-4-nitropyridine-2-carbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 112753916-methyl-4-nitropicolinic acidYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 10.9 g (66.8 mmol) of 6-Methyl-4-nitro-pyridine-2-carbonitrile in 60 ml of 90% sulfuric acid was heated at 120° C. for 2 h and then allowed to cool to room temperature. A solution of 12.2 g (69.0 mmol, 2.65 equiv.) of sodium nitrite in 22 ml of water was added dropwise over a period of 30 min maintaining the temperature between 12-15° C. The reaction was stirred for 30 min at room temperature and then for 1 h at 80° C. The solution was allowed to cool to room temperature and poured onto 150 g of crushed ice. After stirring the yellow solution for 10 min, 200 ml of water were added whereby precipitation occurs. The product is filtered, washed with a small amount of water and dried in vaccuo to yield the title compound as a light yellow crystalline solid (11.2 g, 92%), MS (ISP): m/e=183.1 (M+H)+.

Workup

  1. temperaturemaintaining the temperature between 12-15° C
  2. waitfor 1 h at 80° C
  3. temperatureto cool to room temperature
  4. stirringAfter stirring the yellow solution for 10 min
  5. customwhereby precipitation
  6. filtrationThe product is filtered
  7. washwashed with a small amount of water
  8. customdried in vaccuo

Sources & evidence

ORD record
ord-403cbf7ece294b6f9f616d7882c1f9c6
Source dataset
uspto-grants-2011_05
Patent number
US07951824B2

Reaction notes

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