Ammonia → 6-Fluoro-3-nitropyridine-2-carboxamide

HRID 2256100Notes

Reaction equation

HRID 2256100 reaction equation
[C:1]([C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]([F:12])[N:4]=1)#[N:2].N.[OH:14]S(O)(=O)=O>>[F:12][C:5]1[N:4]=[C:3]([C:1]([NH2:2])=[O:14])[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 108448072-Cyano-6-fluoro-3-nitropyridine

Product 1

HCID 105355166-Fluoro-3-nitropyridine-2-carboxamideYield 61%

Procedure

A solution of 2-cyano-6-fluoro-3-nitropyridine (1.40 g, 8.39 mmol) in 90% H2SO4 (30 mL) is warmed at 70° C. for 90 min, then cooled, poured onto ice and basified with conc. ammonia. Extraction with EtOAc and workup gives 6-fluoro-3-nitropyridine-2-carboxamide (0.94 g, 61%). 1HNMR (CDCl3) δ 8.70 (1H, dd, J=8.9, 6.5 Hz), 8.30, 8.03 (1H, 1H, brs), 7.62 (1H, dd, J=8.9, 2.9 Hz).

Workup

  1. temperaturecooled
  2. extractionExtraction with EtOAc and workup

Sources & evidence

ORD record
ord-8a8f6d38f19b4bf49f960d3a4e2983a2
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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