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

HRID 84584

反応式

HRID 84584 の反応式
[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]

参加物

6

反応物 5

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

生成物 1

HCID 57900098Methyl 5-hydroxy-6-iodopyridine-3-carboxylate収率 81.2%

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-b7932e253f8748e3bb9398fb6e80e7a5
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

関連ノート

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