Nitric Acid → 6-Chloro-2,4-dihydroxy-5-methyl-3-nitropyridine

HRID 11370Notes

Reaction equation

HRID 11370 reaction equation
Cl.[Cl:2][C:3]1[NH:8][C:7](=[O:9])[CH:6]=[C:5]([OH:10])[C:4]=1[CH3:11].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[Cl:2][C:3]1[NH:8][C:7](=[O:9])[C:6]([N+:12]([O-:14])=[O:13])=[C:5]([OH:10])[C:4]=1[CH3:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 546976656-Chloro-4-hydroxy-5-methyl-1,2-dihydropyridin-2-one hydrochloride

Product 1

HCID 547233796-Chloro-2,4-dihydroxy-5-methyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

6-Chloro-4-hydroxy-5-methyl-1H-pyridin-2-one hydrochloride (64 g) was dissolved in sulfuric acid (325 mL) while cooling in an ice bath. Nitric acid was added dropwise over a period of 90 minutes. The reaction mixture was allowed to stir for an additional 30 minutes and then it was poured into ice water (2 L). The resulting precipitate was isolated by filtration, washed with water and then dried to provide 42.5 g of 6-chloro-4-hydroxy-5-methyl-3-nitro-1H-pyridin-2-one as a light yellow solid.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d966ca48e2fb4cd1b175e12286698793
Source dataset
uspto-grants-2006_08
Patent number
US07098221B2

Reaction notes

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