Water → 1-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanone

HRID 889547

Reaction equation

HRID 889547 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[NH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[N:16]=[C:10]([C:6]1[N:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][CH:7]=1)[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 707902,6-DiacetylpyridineHCID 1130332-Chloro-4,6-dimethylaniline

Product 1

HCID 594646241-{6-[1-(2-Chloro-4,6-dimethylphenylimino)ethyl]pyridin-2-yl}ethanoneYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 g of 2,6-diacetylpyridine (0.0613 mol), 9.54 g of 2-chloro-4,6-dimethylaniline (0.0613 mol) and 0.6 g of p-toluenesulfonic acid were heated under reflux on a water separator in 400 ml of toluene for 90 min. The solvent was distilled off completely and the residue was recrystallized from 50 ml of isopropanol. 5.66 g (0.019 mol) of 1-{6-[1-(2-chloro-4,6-dimethyl-phenylimino)ethyl]pyridin-2-yl}ethanone were obtained in a yield of 31%.

Workup

  1. distillationThe solvent was distilled off completely
  2. customthe residue was recrystallized from 50 ml of isopropanol

Sources & evidence

ORD record
ord-e4cca4b4d63d4b6c9ea78ea7da278edc
Source dataset
uspto-grants-2012_08
Patent number
US08252875B2

Linked notes

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