Water → 2-Hydroxy-5-(pyridin-3-yl)pyridine-3-carboxylic acid

HRID 28251Notes

Reaction equation

HRID 28251 reaction equation
[O:1]=[C:2]1[NH:9][CH:8]=[C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[C:3]1[C:4]#N.S(=O)(=O)(O)O.[OH-:21].[Na+].[OH2:23]>>[O:1]=[C:2]1[NH:9][CH:8]=[C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[C:3]1[C:4]([OH:23])=[O:21]

Participants

5

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 13560454HCID 13560454, compound

Product 1

HCID 233397872-Hydroxy-5-(pyridin-3-yl)pyridine-3-carboxylic acid

Procedure

A mixture containing 41 g. of 1,2-dihydro-2-oxo-5-(3-pyridinyl)nicotinonitrile and 410 ml. of 50% aqueous sulfuric acid was refluxed for two hours and then poured into 1.5 kg. of a mixture of ice and water. The acidic mixture was neutralized with 35% aqueous sodium hydroxide solution and the mixture cooled. The separated solid was collected, washed with water and dried in vacuo at 80° C. to yield 47 g. of 1,2-dihydro-2-oxo-5-(3-pyridinyl)nicotinic acid which was used directly without further purification in the next step described below as Example C-2.

Workup

  1. additionA mixture containing 41 g
  2. additionpoured into 1.5 kg
  3. temperaturethe mixture cooled
  4. customThe separated solid was collected
  5. washwashed with water
  6. customdried in vacuo at 80° C.
  7. customto yield 47 g
  8. customof 1,2-dihydro-2-oxo-5-(3-pyridinyl)nicotinic acid which was used directly without further purification in the next step

Sources & evidence

ORD record
ord-ef8a93423f914bdb968f6256907951a3
Source dataset
uspto-grants-1980_09
Patent number
US04225715

Reaction notes

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