2-Pyridinecarboxaldehyde → Bis(6-methyl-2-pyridyl) diketone

HRID 1669640Notes

Reaction equation

HRID 1669640 reaction equation
N1C=CC=CC=1C=O.CC1N=C(CO)C=CC=1.[OH:18][CH:19]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=1)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=1)=[O:21].[OH:36][CH:37]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=1)[C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH3:46])[N:41]=1)=[O:39]>>[CH3:35][C:31]1[N:30]=[C:29]([C:19](=[O:18])[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[N:23]=2)=[O:21])[CH:34]=[CH:33][CH:32]=1.[N:48]1[CH:49]=[CH:50][CH:51]=[CH:52][C:47]=1[C:37](=[O:36])[C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH3:46])[N:41]=1)=[O:39]

Participants

6

Reactant 4

HCID 142732-PyridinecarboxaldehydeHCID 707366-Methyl-2-pyridylmethanolHCID 979272-Hydroxy-1,2-bis(6-methyl-2-pyridinyl)ethanoneHCID 24763988HCID 24763988, compound

Product 2

HCID 81128Bis(6-methyl-2-pyridyl) diketoneHCID 24764031HCID 24764031, compound

Procedure

In addition, in the reaction between 2-pyridinecarboxaldehyde with (6-methylpyridine-2-yl)methanol shown below as reaction 5, the main products obtained are keto-enol compounds: 2-hydroxy-1,2-bis(6-methyl-2-pyridyl)-1-ethanone and 2-hydroxy-1-(6-methyl-2-pyridyl)-2-(2-pyridyl)-1-ethanone. Subsequent treatment with solvent produces 1,2-bis(6-methylpyridine-2-yl)ethane-1,2-dione and 1-(pyridine-2-yl)-2-(6-methylpyridine-2-yl)ethane-1,2-dione and in a much lesser quantity 1,2-bis(6-methylpyridine-2-yl)ethene-1,2-diol (M. J. Percino, V. M. Chapela, O. Urzua, H. Toribio, C. Rodriguez-Barbarin Journal of Chemical Research, (2007), 187).

Workup

  1. customshown below as reaction 5
  2. customthe main products obtained

Sources & evidence

ORD record
ord-3b882a22581f4d64b3f2b8f4dd2fb0b1
Source dataset
uspto-grants-2011_08
Patent number
US07989583B2

Reaction notes

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