1-Chloro-2-nitrobenzene → HCID 20037878, Verbindung

Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.Cl[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>C(O)CCC>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)([O-:18])=[O:17]

Komponenten

Versuchsvorschrift

A mixture of 65 parts of 3-pyridinemethanamine, 94 parts of 1-chloro-2-nitrobenzene, 80 parts of sodium carbonate and 800 parts of 1-butanol is stirred and refluxed over week-end. The reaction mixture is cooled, filtered and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 33 parts (23%) of N-(2-nitrophenyl)-3-pyridinemethanamine.