Water → 5-Methylpicolinonitrile

HRID 632022

반응식

HRID 632022 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[C-:9]#[N:10].[Na+].O>CS(C)=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]#[N:10])=[N:3][CH:4]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 8929Sodium CyanideHCID 27746352-Fluoro-5-methylpyridine

생성물 1

HCID 741835-Methylpicolinonitrile수율 30.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 2-fluoro-5-methylpyridine (CAN: 2369-19-9, 10 g, 90 mmol) and sodium cyanide (8.8 g, 180 mmol) in DMSO (15 mL) was heated to 150° C. for 48 h. Then water was added, the resulting mixture was extracted with ethyl acetate (3×50 mL) and the combined extracts were washed with sodium hypochlorite solution and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 40 g, 10% ethyl acetate in petroleum ether) to yield the title compound (3.2 g, 27 mmol, 30.1%) as yellow solid; MS (EI): m/e=119.1 [M+H]+.

후처리

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×50 mL)
  2. washthe combined extracts were washed with sodium hypochlorite solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel, 40 g, 10% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-94eb4c8212f740ca89f8f222a1a76071
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321727B2

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