Chlorosuccinimide → 6-Chloro-5-hydroxynicotinonitrile

HRID 1483731

반응식

HRID 1483731 반응식
[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

참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 153421425-Hydroxypyridine-3-carbonitrile

생성물 1

HCID 866364556-Chloro-5-hydroxynicotinonitrile수율 36%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
107 °C

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-aecb426368ad4c86b4b5c83defbdc7a2
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416146B2

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