3-Ethylpyridine → 3-Ethylpyridine

Reaction equation

[CH2:1]([C:3]1[CH:4]=[CH:5][C:6](=O)[N:7](C2C=CC=CC=2)[CH:8]=1)[CH3:2].[CH2:16]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH3:17]>C(O)(=O)CCCCCCC/C=C\CCCCCCCC>[NH2:20][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=1.[CH2:16]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH3:17]

Participants

Procedure

In said first reaction scheme, we have found that 5-ethyl-1-phenyl-2-(1H)-pyridone can be made from 3-ethyl pyridine (available from Sigma-Aldrich Corporation, St. Louis, Mo.) which is reacted with NaNH2 in presence of a small amount of oleic acid as a catalyst to speed up the reaction. A general reaction scheme for obtaining 2-amino-5-ethyl pyridine isomer from 3-ethylpyridine is provided in U.S. Pat. No. 5,003,069 to McGill et al, “Chichibabin Reaction,” at Example 12. U.S. Pat. No. 5,003,069 is herein incorporated by reference as if fully set forth herein. In this reaction 3-ethyl pyridine (I) is converted to 2-amino-5-ethylpyridine (II) as well as 2-amino-3-ethylpyridine(III).