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

HRID 620094Notes

Reaction equation

HRID 620094 reaction equation
[O:1]=[C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1.[I:12]N1C(=O)CCC1=O>C(Cl)Cl>[I:12][C:5]1[CH:6]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:2](=[O:1])[NH:3][CH:4]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 579028Methyl 2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 2764465Methyl 5-iodo-2-oxo-1,2-dihydropyridine-3-carboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing 19.48 g of methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate and 36.15 g of N-iodosuccinimide in 500 ml of anhydrous methylene chloride is heated at reflux under a nitrogen atomosphere in the dark for 48 hours. The reaction mixture is concentrated to 150 ml under reduced pressure and the solid which forms is collected by filtration and washed with small portions of cold methylene chloride and benzene to give 16.59 g (47%) of methyl 5-iodo-2-oxo-1,2-dihydro-3-pyridinecarboxylate as a pale yellowish solid. This material is sufficiently pure for the next reaction; its properties upon recrystallization from ethyl acetate are as follows: m.p. 190°-192° C.; NMR (DMSO-d6, 300 MHz) delta 3.71 (s, 3H), 7.93 (d, 1H, J=2.26 Hz), 8.10 (d, 1H, J=2.26 Hz), IR (KBr) 2500-3050 (broad), 1725, 1630, 1585, 1475, 1425, 1320, 1260, 1235, 1180, 1150, 1105, 1065, 965, 875 and 800 cm-1M/S (279, M+), 247, 127 and 93.

Workup

  1. temperatureis heated
  2. temperatureat reflux under a nitrogen atomosphere in the dark for 48 hours
  3. concentrationThe reaction mixture is concentrated to 150 ml under reduced pressure
  4. filtrationthe solid which forms is collected by filtration
  5. washwashed with small portions of cold methylene chloride and benzene

Sources & evidence

ORD record
ord-27d5d305e56b42a5b252a99a814dddaa
Source dataset
uspto-grants-1989_04
Patent number
US04818819

Reaction notes

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