Ethanol → Ethyl 3-aminopyridine-2-carboxylate

HRID 408829

反応式

HRID 408829 の反応式
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:11][CH2:12]O>S(=O)(=O)(O)O>[NH2:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 702EthanolHCID 738363-Aminopicolinic acid

生成物 1

HCID 565054Ethyl 3-aminopyridine-2-carboxylate

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

A mixture of 3-aminopyridine-2-carboxylic acid (6.4 g, 46.3 mmol) in 26 mL of EtOH and 8 mL of concentrated sulfuric acid is heated to reflux for 2 days. After cooling, the mixture is concentrated to about 15-20 mL and poured into 20 g of ice. The mixture is basified to pH 8-9 with concentrated NH4OH while cooling in an ice bath. The resulting brown precipitate is filtered off, and the filtrate is extracted with ether (4×60 mL). The combined ether extracts are washed with brine (4×60 mL), dried (Na2SO4), filtered, and evaporated to give a yellow/brown solid. This solid is combined with that from the above filtration and the whole is triturated with cold ether to give the title compound as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 8.08 (1H, m), 7.21 (1H, m), 7.03 (1H, m), 5.74 (2H, bs), 4.44 (2H, q, J 7.2, 6.9), 1.45 (3H, t, J 6.9).

後処理

  1. temperatureis heated
  2. temperatureto reflux for 2 days
  3. temperatureAfter cooling
  4. concentrationthe mixture is concentrated to about 15-20 mL
  5. additionpoured into 20 g of ice
  6. temperaturewhile cooling in an ice bath
  7. filtrationThe resulting brown precipitate is filtered off
  8. extractionthe filtrate is extracted with ether (4×60 mL)
  9. washThe combined ether extracts are washed with brine (4×60 mL)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated
  13. customto give a yellow/brown solid
  14. filtrationfrom the above filtration
  15. customthe whole is triturated with cold ether

出典と根拠

ORDレコード
ord-3f6be215318b4656a3a63d88c54143b3
出典データセット
uspto-grants-2014_06
特許番号
US08759361B2

関連ノート

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