3-Ethylpyridine → 3-Ethylpyridine

HRID 417795Notes

Reaction equation

HRID 417795 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

5

Reactant 2

HCID 108233-EthylpyridineHCID 101303775-Ethyl-1-phenyl-1H-pyridin-2-one

Product 2

HCID 108233-EthylpyridineHCID 98127775-Ethylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 445639Oleic AcidCatalyst

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).

Workup

  1. customIn said first reaction scheme, we
  2. customthe reaction
  3. customA general reaction scheme

Sources & evidence

ORD record
ord-a91e2bdc326949c5965b6b68c6e11de4
Source dataset
uspto-grants-2012_01
Patent number
US08093210B2

Reaction notes

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