Hydrochloric Acid → 3-Chloro-5-nitro-2(1H)-pyridinone

HRID 464624

Reaction equation

HRID 464624 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7](=[O:10])[NH:8][CH:9]=1)([O-:3])=[O:2].Cl.[Cl:12]([O-])(=O)=O.[K+]>O>[Cl:12][C:6]1[C:7](=[O:10])[NH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 794535-Nitropyridin-2-olHCID 6426889Potassium Chlorate

Product 1

HCID 3362893-Chloro-5-nitro-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Nitro-2-pyridone (Aldrich Chemical Company) (100 g, 0.71 mol) was added to 1 liter conc. HCl at room temperature, followed by the dropwise addition of a solution of potassium chlorate (87.5 g, 0.71 mol) in 1.2 liter water. A solid material formed during the addition. The mixture was stirred overnight, filtered, and the collected material recrystallized from 50 percent aqueous ethanol. The yield was 77.2 g, 62 percent, m.p. 196°-198° C.

Workup

  1. customA solid material formed during the addition
  2. filtrationfiltered
  3. customthe collected material recrystallized from 50 percent aqueous ethanol

Sources & evidence

ORD record
ord-14f5395969a04bf0b5ae561b9969b5b2
Source dataset
uspto-grants-1985_10
Patent number
US04548888

Linked notes

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