2-(p-Tolyl)pyridine → 4-Pyridin-2-ylbenzaldehyde

HRID 1857789Notes

Reaction equation

HRID 1857789 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:3][CH:2]=1.C([O:18]C([NH:21][N:22]=[CH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[CH:26][CH:25]=1)=O)(C)(C)C.N1C=CC=CC=1C1C=CC(C=NN)=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[N:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:27]1[CH:28]=[CH:29][C:24]([CH:23]=[N:22][NH2:21])=[CH:25][CH:26]=1.[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:5]=[CH:6][C:1]([CH:13]=[O:18])=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 782192-(p-Tolyl)pyridineHCID 90495Di-tert-butyl dicarbonateHCID 533949851,1-Dimethylethyl 2-[[4-(2-pyridinyl)phenyl]methylene]hydrazinecarboxylateHCID 679245134-(Pyridin-2-yl)benzaldehyde hydrazone

Product 2

HCID 15152404-Pyridin-2-ylbenzaldehydeHCID 679245134-(Pyridin-2-yl)benzaldehyde hydrazone

Procedure

The present inventors have found that 4-(pyridin-2-yl)benzaldehyde can be produced economically by reacting a salt of 2-(4-bromomethylphenyl)pyridine, 2-(4-dibromomethylphenyl)pyridine or a salt thereof, all of which being novel compounds, with hexamethylenetetramine and water, and further that a salt of 2-(4-bromomethylphenyl)pyridine, 2-(4-dibromomethylphenyl)pyridine and a salt thereof can be obtained by reacting a salt of 2-(4-tolyl)pyridine with a brominating agent. In addition, they have found that N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine can be produced more economically and easily by reacting 4-(pyridin-2-yl)benzaldehyde hydrazone with di-tert-butyl dicarbonate, and that 4-(pyridin-2-yl)benzaldehyde hydrazone can be obtained from 4-(pyridin-2-yl)benzaldehyde.

Workup

  1. customcan be produced more economically

Sources & evidence

ORD record
ord-7a1ca22266a3466fb98ca3ea57d31c15
Source dataset
uspto-grants-2000_11
Patent number
US06147218

Reaction notes

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