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

HRID 1844123Notes

Reaction equation

HRID 1844123 reaction equation
[F: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>[F: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 27629063-Fluoro-5-hydroxypyridine

Product 1

HCID 673878005-Fluoro-2-nitropyridin-3-ol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

With ice cooling, 5 g of 5-fluoropyridin-3-ol (44 mmol, 1 equivalent) were dissolved in 43 ml of concentrated sulphuric acid, and 2.8 ml of concentrated nitric acid were added at 0° C. over a period of 5 min. The reaction was warmed to RT and stirred overnight. The mixture was added to 100 g of ice and stirred for 30 min. The solid formed was filtered off and dried under reduced pressure. This gave 5.6 g (81% of theory) of the title compound which was used without further purification for the next reaction.

Workup

  1. stirringstirred for 30 min
  2. customThe solid formed
  3. filtrationwas filtered off
  4. customdried under reduced pressure
  5. customThis gave 5.6 g (81% of theory) of the title compound which was used without further purification for the next reaction

Sources & evidence

ORD record
ord-f8555f48e04b41b3ac6e08c0612a0771
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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