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

HRID 391557Notes

Reaction equation

HRID 391557 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-57750f342fa042cd87a05a8a05b0a5ec
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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