Ethanol → Ethyl 3-Aminoisonicotinate

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

反応物 5

HCID 702Ethanol

HCID 962Water

HCID 1118Sulfuric Acid

HCID 10340Sodium Carbonate

HCID 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)+.