Water → HCID 59598372, compound

HRID 2266381Notes

Reaction equation

HRID 2266381 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4](=[O:14])[C:3]=1[C:15]([O:17]C)=[O:16].O.[OH-].[Na+]>O1CCOCC1>[I:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4](=[O:14])[C:3]=1[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59598367HCID 59598367, compound

Product 1

HCID 59598372HCID 59598372, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of methyl 4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate (2.34 g, 6.59 mmol) in dioxane (39 mL) was added water (12 mL) followed by sodium hydroxide 6M solution (4.39 ml, 26.4 mmol). The reaction mixture was heated at 50° C. for 4 h. LCMS analysis of an aliquot showed the reaction was complete. The reaction mixture was cooled to room temperature and concentrated in vacuo. Water was added, and the pH was adjusted to ˜3 with 6M aqueous hydrochloric acid solution. The solid formed was isolated by filtration and was dried under high vacuum overnight to give 4-iodo-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid (1.79 g, 5.25 mmol, 80% yield), which was used without further purification. MS (ESI pos. ion) m/z: 364 (M+Na). Calc'd exact mass for C12H81NO3: 341.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionWater was added
  4. customThe solid formed
  5. customwas isolated by filtration
  6. customwas dried under high vacuum overnight

Sources & evidence

ORD record
ord-174f6d6d922842da8bb7c70f024c5281
Source dataset
uspto-grants-2010_12
Patent number
US07858623B2

Reaction notes

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