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

HRID 2401628Notes

Reaction equation

HRID 2401628 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 reaction mixture was stirred into an ice/water mixture and it was 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. stirringwas stirred for another 30 min The solid
  2. filtrationwas 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-bf28d5d71e43411b89fabc80ac6969e6
Source dataset
uspto-grants-2014_08
Patent number
US08796305B2

Reaction notes

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