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

HRID 1961475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1961475
[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]

Komponenten

9

Edukt 5

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

Produkt 1

HCID 177501772-Amino-5-iodopyridine-3-carbaldehydeAusbeute 538,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c2d8d86da6a94752b68f2c0c63748710
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415333B2

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