Chlorosuccinimide → 6-Chloro-5-hydroxynicotinonitrile

HRID 1255723

反応式

HRID 1255723 の反応式
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8].[Cl:10]N1C(=O)CCC1=O>C(#N)C>[Cl:10][C:3]1[C:2]([OH:1])=[CH:9][C:6]([C:7]#[N:8])=[CH:5][N:4]=1

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 153421425-Hydroxypyridine-3-carbonitrile

生成物 1

HCID 866364556-Chloro-5-hydroxynicotinonitrile収率 36%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
107 °C

実験手順

A mixture of 5-hydroxy-nicotinonitrile (2.0 g, 16.66 mmol), and N-chlorosuccinimide (3.3 g, 25.0 mmol) in acetonitrile (33 mL) was heated in a sealed tube at 107° C. overnight. Acetonitrile was removed under reduced pressure, the residue was diluted with EtOAc (100 mL). The organic layer was washed with water (10 mL) and brine (2×10 mL), dried over Na2SO4, filtered, and concentrated to give brown oil. Purification was accomplished by flash chromatography on silica gel using 20-80% EtOAc/hexanes gradient elution to yield the title compound (0.55 g, 36%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.70 (s, 1H), 8.35 (d, J=2.0 Hz, 1H), 7.67 (d, J=2.0 Hz, 1H); MS (ES) m/z: 153 (M−1)−.

後処理

  1. customAcetonitrile was removed under reduced pressure
  2. additionthe residue was diluted with EtOAc (100 mL)
  3. washThe organic layer was washed with water (10 mL) and brine (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give brown oil
  8. customPurification
  9. washwas accomplished by flash chromatography on silica gel using 20-80% EtOAc/hexanes gradient elution

出典と根拠

ORDレコード
ord-743d6628b8ff4fa486c9944e32cd978f
出典データセット
uspto-grants-2013_06
特許番号
US08461135B2

関連ノート

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