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

HRID 598051Notes

Reaction equation

HRID 598051 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[OH-].[Na+].O[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=1.Cl>>[CH3:11][N:12]1[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:7]1=[O:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178526703HCID 178526703, compound

Product 1

HCID 2958661-methyl-5-nitro-2(1H)-pyridinoneYield 29.8%

Conditions

Temperature
25 °C

Procedure

To a mixture containing 20.0 ml (211.40 mmol) of dimethyl sulfate and 45 ml of 3N sodium hydroxide was added 4.00 g (28.55 mmol) of 2-hydroxy-5-nitropyridine in portions over 15 min. After complete addition, the reaction was allowed to stir at 25° C. overnight. The reaction was acidified with 1N HCl and the solids filtered, washed with ethanol and dried to afford 1.31 g (29.77%) of product.

Workup

  1. additionAfter complete addition
  2. filtrationthe solids filtered
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-4f3e7d02d2ff4146bef87d83b55468e4
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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