Methanol → Methyl 6-methylpyridine-2-carboxylate

HRID 643774

反応式

HRID 643774 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[CH3:16][O:9][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:10]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 702826-Methylpyridine-2-carboxylic acid

生成物 1

HCID 73022Methyl 6-methylpyridine-2-carboxylate収率 59%

実験手順

A mixture of 6-methyl-pyridine-2-carboxylic acid (10 g, 72.9 mmol) and concentrated sulfuric acid (3.5 mL) in methanol (300 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was poured into saturated aqueous sodium hydrogen carbonate (250 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried (magnesium sulfate), filtered, and evaporated to give 6-methyl-pyridine-2-carboxylic acid methyl ester (6.5 g, 59%) as a colorless oil. 1HNMR (CDCl3): δ 7.97 (d, J=7.6 Hz, 1H), 7.73 (dd, J=7.6 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H), 4.01 (s, 3H), 2.67 (s, 3H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was poured into saturated aqueous sodium hydrogen carbonate (250 mL)
  5. extractionextracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic layers were dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-81858029d6b741388925c417aa43d252
出典データセット
uspto-grants-2010_04
特許番号
US07700632B2

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