Iodine → Methyl 6-amino-5-iodo-2-(methyloxy)-3-pyridinecarboxylate

HRID 489804Notes

Reaction equation

HRID 489804 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[I:14]I.O>CN(C)C=O.C(OCC)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[I:14]

Participants

6

Reactant 3

HCID 807IodineHCID 962WaterHCID 11159681Methyl 6-amino-2-methoxynicotinate

Product 1

HCID 22262635Methyl 6-amino-5-iodo-2-(methyloxy)-3-pyridinecarboxylateYield 79.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 6-amino-2-(methyloxy)-3-pyridinecarboxylate (2.1 g, 11.8 mmol) and iodine (15 g, 59 mmol) in N,N-dimethylformamide (50 ml) was stirred overnight at room temperature. The mixture was poured into water (200 ml) and extracted with ethyl acetate (50 ml×2). The combined organic layer was washed with saturated sodium bicarbonate, 20% aqueous thiosulphate and brine, dried over magnesium sulfate, and concentrated in vacuo gave a brown solid. The residue was suspended in diethyl ether and collected by filtration to afford 2.9 g (79%) of the title compound as a pale brown solid.

Workup

  1. extractionextracted with ethyl acetate (50 ml×2)
  2. washThe combined organic layer was washed with saturated sodium bicarbonate, 20% aqueous thiosulphate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customgave a brown solid
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-04f8aaed5660453993c189703e027da9
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

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