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

HRID 2275759Notes

Reaction equation

HRID 2275759 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, at 0° C., 2.8 ml of concentrated nitric acid were added over a period of 5 min. The reaction was warmed to RT, and stirring was continued overnight. The mixture was added to 100 g of ice and stirred for 30 min. The solid obtained was filtered off and dried under reduced pressure. This gave 5.6 g (81% of theory) of the title compound, which were used without further purification for the next reaction.

Workup

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

Sources & evidence

ORD record
ord-f94662b754d24aaebb355ee9724104c2
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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