N-Iodosuccinimide → Methyl 5-iodo-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 416572Notes

Reaction equation

HRID 416572 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[OH:10].[I:12]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([I:12])[CH:7]=[N:6][C:5]=1[OH:10]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178498115HCID 178498115, compound

Product 1

HCID 2764465Methyl 5-iodo-2-oxo-1,2-dihydropyridine-3-carboxylateYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxynicotinic acid methyl ester (3-067-02) (20 g) in methylene chloride (500 mL) was added N-iodosuccinimide (NIS, 38 g) at room temperature, and the reaction mixture was heated under reflux for 16 h, and evaporated. To the residue was added ethyl acetate (200 mL) and the reaction mixture was heated under reflux for 2 h. The insoluble solid was filtered to give 2-hydroxy-5-iodonicotinic acid methyl ester (3-067-03) (30 g, 81%) as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 16 h
  3. customevaporated
  4. additionTo the residue was added ethyl acetate (200 mL)
  5. temperaturethe reaction mixture was heated
  6. temperatureunder reflux for 2 h
  7. filtrationThe insoluble solid was filtered

Sources & evidence

ORD record
ord-76947b6239e94fe2a73f48181b8c0ee7
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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