Iodine → 2-Amino-5-iodopyridine-3-carbaldehyde

HRID 1961475Notes

Reaction equation

HRID 1961475 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[I:10](O)(=O)(=O)=O.II.[O-]S([O-])(=S)=O.[Na+].[Na+].[OH-].[Na+]>C(O)(=O)C.O.OS(O)(=O)=O>[NH2:1][C:2]1[N:9]=[CH:8][C:7]([I:10])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

9

Reactant 5

HCID 807IodineHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 65185Metaperiodic acidHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 177501772-Amino-5-iodopyridine-3-carbaldehydeYield 538.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

2-Aminonicotinaldehyde (515 mg, 4.22 mmol), periodic acid (144.1 mg, 0.63 mmol) and iodine (460.2 mg, 0.43 mmol) were dissolved in a mixture of acetic acid (12.0 ml), H2O (0.6 ml) and H2SO4 (0.1 ml). The mixture was heated to 80° C. for 4 h. Then it was poured into Na2S2O3 (10% aq. solution), neutralized with NaOH (2N aq. solution) and extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography; Pet. Ether, EtOAc (4:1→1:1) affording 842 mg (80%) the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-c2d8d86da6a94752b68f2c0c63748710
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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