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Sodium Methoxide → 6-Methoxy-2-methylpyridine-3-carbonitrile

HRID 574117
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HRID 574117 반응식
[CH3:1][O-:2].[Na+].Cl[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH3:13])[N:6]=1>CO>[CH3:1][O:2][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([CH3:13])[N:6]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 10942334Sodium MethoxideHCID 123877376-Chloro-2-methylnicotinonitrile

생성물 1

HCID 137499186-Methoxy-2-methylpyridine-3-carbonitrile수율 87%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Sodium methoxide (20 g, 0.4 mol) was added to a solution of 6-chloro-2-methylnicotinonitrile (132, 10 g, 66 mmol) in methanol (150 mL), and the mixture was heated at reflux for 1.5 h and cooled to room temperature. The precipitate was removed by filtration, and the filtrate was concentrated to dryness. The crude solid was redissolved in chloroform; and the resulting solution was filtered through a layer of silica gel, washing with extra portions of chloroform. The combined filtrates were evaporated to dryness to yield 41 (8.3 g, 87%): mp 81-82° C. (lit. (Synthesis 1991, 894-896) mp 80-80.5° C.). 1HNMR (300 MHz, CDCl3) δ 7.66 (d, J=8.5 Hz, 1H), 6.59 (d, J=8.5 Hz, 1H), 3.94 (s, 3H), 2.62 (s, 3H).

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후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe crude solid was redissolved in chloroform
  6. filtrationand the resulting solution was filtered through a layer of silica gel
  7. washwashing with extra portions of chloroform
  8. customThe combined filtrates were evaporated to dryness

출처 및 근거

ORD 기록
ord-563b472e7d5146a09ad5c8703d4944be
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09034870B2

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