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

HRID 84584

Reaktionsgleichung

Reaktionsgleichung von HRID 84584
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[N:6][CH:5]=1.O1CCCC1.O.C(=O)([O-])[O-].[Na+].[Na+].[I:24]I>>[OH:10][C:8]1[C:7]([I:24])=[N:6][CH:5]=[C:4]([CH:9]=1)[C:3]([O:2][CH3:1])=[O:11]

Komponenten

6

Edukt 5

HCID 807IodineHCID 962WaterHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Produkt 1

HCID 57900098Methyl 5-hydroxy-6-iodopyridine-3-carboxylateAusbeute 81,2 %

Versuchsvorschrift

To solution of 5-hydroxy-nicotinic acid methyl ester (2.50 g, 16.3 mmol) in tetrahydrofuran (50.0 mL, 616 mmol)/water (50.0 mL, 2780 mmol) was added sodium carbonate (5.19 g, 49.0 mmol) and iodine (10.4 g, 40.8 mmol). The reaction mixture was stirred at room temperature 4h. The aqueous layer containing product was separated and wash with hexane. The organic layer was neutralized to pH 7 with HCl, extracted EtOAc 4×. The combined organic layers was dried Na2SO4, concentrated. The crude product was purified by flash chromatography (EtOAc/DCM) (eluted at 40 EtOAc) to give methyl 5-hydroxy-6-iodonicotinate (81.2%) MS: (ESI+) 280.0

Aufarbeitung

  1. additionThe aqueous layer containing product
  2. customwas separated
  3. washwash with hexane
  4. extractionextracted EtOAc 4×
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (EtOAc/DCM) (eluted at 40 EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b7932e253f8748e3bb9398fb6e80e7a5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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