Ethanol → Ethyl 3-Aminoisonicotinate

HRID 1655586

反応式

HRID 1655586 の反応式
[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]

参加物

6

反応物 5

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

生成物 1

HCID 2736365Ethyl 3-Aminoisonicotinate

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-552e0642e4f341e1a412afcbe22a791b
出典データセット
uspto-grants-1993_10
特許番号
US05250548

関連ノート

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