Nitric Acid → 5-Chloro-2-nitropyridin-3-ol

HRID 2275764Notes

Reaction equation

HRID 2275764 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[N+:9]([O-])([OH:11])=[O:10]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[C:5]([N+:9]([O-:11])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 187656985-Chloro-2-nitropyridin-3-ol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and, at 0° C., 24 ml of concentrated nitric acid were added slowly. The reaction was warmed to RT, stirred overnight and then stirred into an ice/water mixture and stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound, which were used without further purification for the next reaction.

Workup

  1. stirringstirred for another 30 min
  2. filtrationThe solid was filtered off
  3. washwashed with cold water
  4. customair-dried
  5. customThis gave 33 g (82% of theory) of the title compound, which were used without further purification for the next reaction

Sources & evidence

ORD record
ord-04c52ddfa6034aaa9c587d0030936602
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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