2,4-Dichloro-3,5,6-trimethylpyridine → 4-Chloro-2,3,5-trimethylpyridine

HRID 2231950ノート

反応式

HRID 2231950 の反応式
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6](Cl)[N:5]=[C:4]([CH3:10])[C:3]=1[CH3:11].[H][H]>C(O)C.S(=O)(=O)(O)O.[Pd]>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH3:10])[C:3]=1[CH3:11]

参加物

6

反応物 2

HCID 27791392,4-Dichloro-3,5,6-trimethylpyridineHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 142036064-Chloro-2,3,5-trimethylpyridine収率 78%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 1118Sulfuric Acid溶媒

実験手順

200 g 4,6-dichloro-2,3,5-trimethylpyridine dissolved in 300 ml ethanol and 40 ml conc. sulphuric acid. 2 g 10% Pd/C was used as catalyst. The hydrogen pressure was 2 bar and the hydrogenation was stopped when 1 equivalent of hydrogen had been consumed. After evaporation of alcohol and dilution with water and adjustment of pH to 2.1 the water was extracted with toluene. The toluene contains all starting material and 6-chloro-2,3,5-trimethylpyridine and the water phase 4-chloro-2,3,5-trimethylpyridine and 2,3,5-trimethylpyridine. The pH of the water phase is adjusted to 4.6 and extracted with toluene (3x100 ml). All 4-chloro-2,3,5-trimethylpyridine is in the toluene layer and the 2,3,5-trimethylpyridine in the water. Evaporation of the toluene gave 4-chloro-2,3,5-trimethylpyridine in 78% yield (liquid). NMR: 2×3H, 2,3; 3H, 2,5(s); 1H, 8,25(s). (CDCl3)

後処理

  1. customhad been consumed
  2. customAfter evaporation of alcohol and dilution with water and adjustment
  3. extractionwas extracted with toluene
  4. extractionextracted with toluene (3x100 ml)
  5. customEvaporation of the toluene

出典と根拠

ORDレコード
ord-f3ebc192681442b0aab57f9285dc4b81
出典データセット
uspto-grants-1988_11
特許番号
US04785113

反応ノート

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