N-Iodosuccinimide → 5-Iodo-1-(2-methoxy-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

HRID 524332Notes

Reaction equation

HRID 524332 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:10]([CH3:11])=[CH:9][C:8](=[O:12])[C:7]([C:13]([OH:15])=[O:14])=[CH:6]1.[I:16]N1C(=O)CCC1=O>C(O)(C(F)(F)F)=O.ClCCl.O>[I:16][C:9]1[C:8](=[O:12])[C:7]([C:13]([OH:15])=[O:14])=[CH:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:10]=1[CH3:11]

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 867115801-(2-Methoxyethyl)-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 867115795-Iodo-1-(2-methoxy-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution 1-(2-methoxy-ethyl)-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (150 mg, 0.71 mmol) and N-iodosuccinimide (200 mg, 0.89 mmol) in TFA (1 mL) and dichloromethane (1 mL) is stirred for 5 days at room temperature. The reaction mixture is diluted with water and extracted with dichloromethane. The organic layer is evaporate under reduced pressure. ESI mass spectrum: [M+H]+=338; Retention time HPLC: 0.95 min (Z002_005).

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic layer is evaporate under reduced pressure
  3. custom0.95 min (Z002_005)

Sources & evidence

ORD record
ord-ab92eaeddb074059b5ee0f3aed6c4ac6
Source dataset
uspto-grants-2016_05
Patent number
US09340507B2

Reaction notes

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