Ethanol → HCID 44549262、化合物

HRID 2377046ノート

反応式

HRID 2377046 の反応式
S(=O)(=O)(O)[OH:2].[CH3:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][N:10]=[C:9]([C:16]#N)[CH:8]=1.[CH2:18]([OH:20])[CH3:19]>>[CH3:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][N:10]=[C:9]([C:16]([O:20][CH2:18][CH3:19])=[O:2])[CH:8]=1

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 230001714-Methyl-5-nitropyridine-2-carbonitrile

生成物 1

HCID 44549262HCID 44549262、化合物収率 56%

実験手順

Concentrated sulfuric acid (768 mL) was added slowly to ethanol (1.6 L) with cooling (exothermic reaction!). 4-Methyl-5-nitropyridine-2-carbonitrile (62.4 g, 0.38 mol) was added to the cold solution. After the addition was complete, the solution was refluxed under nitrogen for 2 h. Part of the solvent (500 mL) was removed using an oil pump at 30° C. The remaining thick solution was poured onto ice (1 kg). After stirring for 15 min, the mixture was extracted with ether (2×1 L) and multiple times with dichloromethane. At first, the organic layer was the TOP layer. As the extraction continued, the organic layer changed from the top layer to the bottom layer due to change in density as less ethanol was extracted. The combined organic extracts were dried (magnesium sulfate) and concentrated. Recrystallization from hexanes yielded 44.4 g (56%) of the desired product. 1H NMR (300 MHz, CDCl3) δ ppm 1.46 (t, 3H, J=7.5 Hz), 2.71 (s, 3H), 4.51 (q, 2H, J=7.5 Hz), 8.13 (s, 1H), 9.22 (s, 1H). LCMS: (APCI, M+H+)=209

後処理

  1. temperaturewith cooling
  2. custom(exothermic reaction!)
  3. additionAfter the addition
  4. temperaturethe solution was refluxed under nitrogen for 2 h
  5. customPart of the solvent (500 mL) was removed
  6. customat 30° C
  7. additionThe remaining thick solution was poured onto ice (1 kg)
  8. extractionthe mixture was extracted with ether (2×1 L) and multiple times with dichloromethane
  9. extractionAs the extraction
  10. extractionwas extracted
  11. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  12. concentrationconcentrated
  13. customRecrystallization from hexanes

出典と根拠

ORDレコード
ord-32b6ea71f54949b7a50ee79d0c96740e
出典データセット
uspto-grants-2008_12
特許番号
US07468375B2

反応ノート

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