Hydrochloric Acid → 1-Methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

HRID 1976773Notes

Reaction equation

HRID 1976773 reaction equation
[I-].[CH3:2][N+:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11]C)=[O:10])=[CH:5][CH:4]=1.[OH-:13].[Na+].Cl>O>[CH3:2][N:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=[O:10])=[CH:5][C:4]1=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 129454874-(Methoxycarbonyl)-1-methylpyridin-1-ium iodide

Product 1

HCID 8199231-Methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A solution of N-methyl-4-methoxycarbonylpyridinium iodide (2.00 g, 7.16 mmol) in water (10 mL) at room temperature was treated sequentially with 14M sodium hydroxide (1.0 mL) and 1.8M K3Fe(CN)6 (1.5 mL), stirred for 4 hours, treated again with 1.8M K3Fe(CN)6 once per hour for 4 hours, heated at 55° C. for one hour, cooled to room temperature, and treated with 6M HCl to pH 3. The precipitate was collected, washed with ether and dried under vacuum to provide 1.00 g of the desired product.

Workup

  1. temperaturecooled to room temperature
  2. customThe precipitate was collected
  3. washwashed with ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8c4da58f0dc249f5a86210fcb45b6efe
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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