Ethanol → Ethyl 3-aminopyridine-2-carboxylate

HRID 408829

반응식

HRID 408829 반응식
[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

참가 물질

4

반응물 2

HCID 702EthanolHCID 738363-Aminopicolinic acid

생성물 1

HCID 565054Ethyl 3-aminopyridine-2-carboxylate

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3f6be215318b4656a3a63d88c54143b3
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759361B2

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