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

HRID 1961475ノート

反応式

HRID 1961475 の反応式
[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]

参加物

9

反応物 5

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

生成物 1

HCID 177501772-Amino-5-iodopyridine-3-carbaldehyde収率 538.9%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c2d8d86da6a94752b68f2c0c63748710
出典データセット
uspto-grants-2013_04
特許番号
US08415333B2

反応ノート

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