Iodine → Methyl 6-amino-5-iodopyridine-3-carboxylate

HRID 1099650Notes

Reaction equation

HRID 1099650 reaction equation
[I:1]I.[NH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1.CO.C(Cl)(Cl)Cl>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:3][C:4]1[C:13]([I:1])=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 807IodineHCID 737487Methyl 6-aminonicotinateHCID 21584188Chloroform methanol

Product 1

HCID 15350913Methyl 6-amino-5-iodopyridine-3-carboxylateYield 62.2%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of iodine (3.55 g, 14.0 mmol) in 100 mL absolute ethanol at room temperature was added silver sulfate (4.37 g, 14.0 mmol) and methyl 6-aminonicotinate (1.52 g, 10.0 mmol). After 42 hours the reaction was filtered to isolate a tan precipitate. The solid was heated with 20% MeOH/CHCl3 then cooled to room temperature, filtered, and rinsed with MeOH and CHCl3. The filtrate was evaporated, dissolved in hot MeOH, filtered to remove brownish impurities, and then crystallized from MeOH to give the title compound as a light tan solid (1.73 g, 62%).

Workup

  1. filtrationAfter 42 hours the reaction was filtered
  2. customto isolate a tan precipitate
  3. filtrationfiltered
  4. washrinsed with MeOH and CHCl3
  5. customThe filtrate was evaporated
  6. dissolutiondissolved in hot MeOH
  7. filtrationfiltered
  8. customto remove brownish impurities
  9. customcrystallized from MeOH

Sources & evidence

ORD record
ord-a650341b10704e5c80d18aea93b75530
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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