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

HRID 1008097Notes

Reaction equation

HRID 1008097 reaction equation
O.Cl.[Cl:3][C:4]1[NH:9][C:8](=[O:10])[CH:7]=[C:6]([OH:11])[C:5]=1[CH3:12].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[Cl:3][C:4]1[NH:9][C:8](=[O:10])[C:7]([N+:13]([O-:15])=[O:14])=[C:6]([OH:11])[C:5]=1[CH3:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 547233806-chloro-4-hydroxy-5-methylpyridin-2(1H)-one hydrochloride hydrate

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 6-chloro-4-hydroxy-5-methylpyridin-2(1H)-one hydrochloride hydrate (67.0 g, 0.313 mmol) in concentrated sulfuric acid (335 mL) was cooled to ˜0° C.; nitric acid (19.6 mL of 16 M) was added dropwise over a period of ten minutes. The reaction was stirred for 20 minutes and then poured slowly into 2.5 L of ice water. A yellow precipitate formed, which was isolated by filtration and dried overnight in a vacuum oven at 60° C. to provide 39.7 g of 6-chloro-4-hydroxy-5-methyl-3-nitropyridin-2(1H)-one as a yellow solid.

Workup

  1. customA yellow precipitate formed
  2. customwhich was isolated by filtration
  3. customdried overnight in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-e9575cd09dc34d999be293763822659e
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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