Ethanol → Ethyl 3-Aminoisonicotinate

HRID 1655586

반응식

HRID 1655586 반응식
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].S(=O)(=O)(O)O.O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:23](O)[CH3:24]>>[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH2:23][CH3:24])=[O:9]

참가 물질

6

반응물 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 4595313-Aminoisonicotinic acid

생성물 1

HCID 2736365Ethyl 3-Aminoisonicotinate

실험 절차

A suspension of 3-aminopyridine-4-carboxylic acid (2.00 g, 14.5 mmol), prepared by the method of Crum and Fuchsman, J. Het. Chem. 3, 252 (1966), in ethanol (~4 g) was treated with 4.0 g of sulfuric acid and warmed on a steam bath for 4 hours. After cooling to ambient temperature, water (~40 mL) and solid sodium carbonate were added to basify the solution which was then extracted with chloroform (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue obtained was flash chromatographed on silica gel eluting with 2:1 hexane/ethyl acetate to afford the title compound. 1H NMR (CDCl3, 300 MHz) δ 1.41 (t, J=7 Hz, 3H), 4.37 (q, J=7 Hz, 2H), 7.60 (d, J=6 Hz, 1H), 7.93 (d, J=6 Hz, 1H), 8.19 (s, 1H). MS (DCI/NH3) m/e 167 (M+H)+, 184 (M+H+NH3)+.

후처리

  1. customprepared by the method of Crum and Fuchsman, J
  2. temperaturewarmed on a steam bath for 4 hours
  3. extractionwas then extracted with chloroform (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customchromatographed on silica gel eluting with 2:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-552e0642e4f341e1a412afcbe22a791b
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05250548

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