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

HRID 1265137Notes

Reaction equation

HRID 1265137 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-335c0a926a1a42d0a4d479ece2823a9b
Source dataset
uspto-grants-2003_04
Patent number
US06545016B1

Reaction notes

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