Nitric Acid → HCID 178524577, compound

HRID 1289999Notes

Reaction equation

HRID 1289999 reaction equation
[OH:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.[N+:16]([O-])([OH:18])=[O:17]>>[OH:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([N+:16]([O-:18])=[O:17])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 178418543HCID 178418543, compound

Product 1

HCID 178524577HCID 178524577, compoundYield 65%

Procedure

The nitration of 2-hydroxy-3-carboxypyridine was performed as taught by Winn et al J. Med. Chem, (36) 2676-2688 (1993). In a 250 mL round bottom flask fitted with a stirrer bar and cooling bath was added 150 mL of concentrated sulfuric acid and 17 g of starting material. Then 10 ml of concentrated nitric acid (67%) was added dropwise to the solution over a period of 20 minutes, keeping the reaction temperature at <8° C. The reaction mixture was warmed to room temperature and stirred overnight. The next day the reaction was heated to 70° C. for 90 minutes. The reaction mixture was cooled to 25° C. and poured the reaction mixture into 1 liter of ice/water. The product, which precipitated out of solution, was recrystallized from ethanol. Recovered 18 g of product. Yield=65%.

Workup

  1. customIn a 250 mL round bottom flask fitted with a stirrer bar
  2. temperaturecooling bath
  3. customat <8° C
  4. temperatureThe next day the reaction was heated to 70° C. for 90 minutes
  5. temperatureThe reaction mixture was cooled to 25° C.
  6. customThe product, which precipitated out of solution
  7. customwas recrystallized from ethanol
  8. customRecovered 18 g of product

Sources & evidence

ORD record
ord-2523898a1e8f48d7a1f34c0845ea0f2c
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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