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

HRID 1844127Notes

Reaction equation

HRID 1844127 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 and stirred overnight. The mixture was 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-c994a0bca75b4bbe95bfb209d8931767
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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