Water → 5-Methylpicolinonitrile

HRID 632022

反応式

HRID 632022 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 741835-Methylpicolinonitrile収率 30.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-94eb4c8212f740ca89f8f222a1a76071
出典データセット
uspto-grants-2016_04
特許番号
US09321727B2

関連ノート

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