Nitric Acid → 5-Chloro-2-hydroxy-3-nitropyridine

HRID 66359Notes

Reaction equation

HRID 66359 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:10].[N+:14]([O-])([OH:16])=[O:15]>>[Cl:8][C:5]1[CH:6]=[C:7]([N+:14]([O-:16])=[O:15])[C:2](=[O:10])[NH:3][CH:4]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 661742-Amino-5-chloropyridine

Product 1

HCID 2480485-Chloro-2-hydroxy-3-nitropyridine

Conditions

Temperature
0 °C

Procedure

2-Amino-5-chloropyridine (12.8 g., 0.1 mole) was added to 50 ml. of concentrated sulfuric acid. To this was slowly added with stirring 25 ml. of concentrated nitric acid. After the exothermic reaction subsided, the mixture was cooled and poured onto ice. The precipitate was collected and added to a mixture of 12 ml. of concentrated sulfuric acid and 150 ml. of water. To this solution cooled to 0° C., was added 7 g. of sodium nitrite portionwise and the resulting mixture was allowed to warm spontaneously to room temperature. After cooling the precipitate was collected and recrystallized from dimethyl formamideethanol to give 5-chloro-3-nitro-2-pyridone, m.p. 225-227.

Workup

  1. additionTo this was slowly added
  2. customAfter the exothermic reaction
  3. temperaturethe mixture was cooled
  4. additionpoured onto ice
  5. customThe precipitate was collected
  6. additionadded to a mixture of 12 ml
  7. additionwas added 7 g
  8. temperatureto warm spontaneously to room temperature
  9. temperatureAfter cooling the precipitate
  10. customwas collected
  11. customrecrystallized from dimethyl formamideethanol

Sources & evidence

ORD record
ord-90d477521fc14b17bcd9988ccd067eeb
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Reaction notes

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