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

HRID 1386082Notes

Reaction equation

HRID 1386082 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[N+:9]([O-])([OH:11])=[O:10].[OH-].[Na+]>S(=O)(=O)(O)O>[NH2:1][C:2]1[C:7]([N+:9]([O-:11])=[O:10])=[CH:6][C:5]([F:8])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 217173395-Fluoro-3-nitropyridin-2-amineYield 3.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-amino-5-fluoropyridine (8.6 g, 77 mmol) in conc. sulfuric acid (40 ml) was added dropwise (30 min) fuming nitric acid (3.25 ml, 77 mmol) at a temperature of +3° C. The reaction mixture was stirred at room temperature for 1 h and at +55° C. for 1 h. The mixture was poured onto ice and neutralized with 10 M sodium hydroxide and was extracted with methylene chloride. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified twice by column chromatography on silica gel, using (i) methanol:methylene chloride (1:20) and (ii) diethyl ether:petroleum ether (1:1) as eluent to give the title compound (0.44 g, 3.6%).

Workup

  1. extractionwas extracted with methylene chloride
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified twice by column chromatography on silica gel

Sources & evidence

ORD record
ord-49223f9b38ed493fadf0ba39e6daca5e
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

Loading…