Water → HCID 58117243, compound

HRID 1406404Notes

Reaction equation

HRID 1406404 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[CH:19]=[CH:18][C:17](=[O:20])[NH:16][C:15]=1[CH3:21])=[O:13])[CH3:10].O>C(#N)C>[CH2:9]([O:11][C:12]([C:14]1[CH:19]=[C:18]([I:1])[C:17](=[O:20])[NH:16][C:15]=1[CH3:21])=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 3299500ethyl 2-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate2×

Product 1

HCID 58117243HCID 58117243, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

N-Iodosuccinimide (40 g, 180 mmol) was added to a suspension of intermediate (5b), 2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (18.1 g, 100 mmol) in acetonitrile (400 mL), under a nitrogen atmosphere. The resulting suspension was heated at 95° C. for 5 hours to give an initial orange solution. An off-white precipitate slowly formed. The resulting suspension was allowed to cool and was poured into water (1200 mL) to give an off-white precipitate. The separated by filtration and the solids washed with water (500 mL) to give an off-white powder. The solids were dried in vacuo (60° C.) to give the product as an off-white powder, 28.3 g (92%)

Workup

  1. customto give an initial orange solution
  2. customAn off-white precipitate slowly formed
  3. temperatureto cool
  4. customto give an off-white precipitate
  5. customThe separated by filtration
  6. washthe solids washed with water (500 mL)
  7. customto give an off-white powder
  8. customThe solids were dried in vacuo (60° C.)

Sources & evidence

ORD record
ord-528ccf711f0e4a7caa3e0c18cc37e075
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

Loading…