1,4-Dioxane → 6-Methyl-5-nitropyridine-2-carbaldehyde

HRID 510477노트

반응식

HRID 510477 반응식
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.[O:12]1CCOCC1>>[CH3:1][C:2]1[N:3]=[C:4]([CH:11]=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

참가 물질

3

반응물 2

HCID 312751,4-DioxaneHCID 849582,6-Dimethyl-3-nitropyridine

생성물 1

HCID 30151966-Methyl-5-nitropyridine-2-carbaldehyde수율 37.4%

실험 절차

A solution of 2,6-dimethyl-3-nitropyridine (1.5 g, 9.85 mmol) and SeO2 (1.4 g, 12.81 mmol) in 1,4-dioxane (15 mL) was heated at reflux for 16 h. The reaction mixture was then filtered through Celite and the solvent was evaporated. The crude material obtained was purified by column chromatography (silica: 100-200 mesh, EtOAc:hexane 20-25%) to afford the title compound (0.61 g, 37.4%). δH (CDCl3) 10.09 (s, 1H), 8.39 (d, J=8.3 Hz, 1H), 7.97 (d, J=8.3 Hz, 1H), 2.94 (s, 3H).

후처리

  1. temperatureat reflux for 16 h
  2. filtrationThe reaction mixture was then filtered through Celite
  3. customthe solvent was evaporated
  4. customThe crude material obtained
  5. customwas purified by column chromatography (silica: 100-200 mesh, EtOAc:hexane 20-25%)

출처 및 근거

ORD 기록
ord-9caca7fe79674456bdb2f797ae4b1b15
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096614B2

반응 노트

불러오는 중…