Water → 2-Formylnicotinonitrile

HRID 7154

반응식

HRID 7154 반응식
[C:1]([C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2].O.[Se](=O)=[O:12]>O1CCOCC1>[C:1]([C:3]1[C:4]([CH:9]=[O:12])=[N:5][CH:6]=[CH:7][CH:8]=1)#[N:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 24007Selenium DioxideHCID 47383082-Methylpyridine-3-carbonitrile

생성물 1

HCID 190294752-Formylnicotinonitrile수율 10%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 3-cyano-2-picoline (166 mg, 1.41 mmol) in dioxane (3 mL) was added water (0.2 mL) and selenium(IV) oxide (228 mg, 2.05 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1 then 1:1) to afford the title compound (18 mg, 10%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.69 (dd, 1H, J=9, 6 Hz), 8.20 (d, 1H, J=9 Hz), 9.00 (d, 1H, J=3 Hz), 10.13 (s, 1H).

후처리

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel (Hexanes/ether, 3:1

출처 및 근거

ORD 기록
ord-c91b9e7b100246bd91748a1ae525db65
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084155B2

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