2-Chloro-3-nitropyridine → [2-Chloro-4-(3-nitropyridin-2-ylamino)-phenyl]-acetic acid ethyl ester
Reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11]([O:13][C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[Cl:23])[CH3:12]>CCO.O1CCOCC1>[CH2:11]([O:13][C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:18][C:17]=1[Cl:23])[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 0.600 g of 2-chloro-3-nitro-pyridine (Aldrich) and 0.800 g of (4-amino-2-chloro-phenyl)-acetic acid ethyl ester (see WO 97/21665) in 20 ml of EtOH/dioxane (1:1, v/v) is stirred and refluxed for 72 hours. The mixture obtained is allowed to cool to rt and is concentrated in vacuo. The concentrate obtained is subjected to silica gel column chromatography. A solid is obtained which is triturated with Et2O. [2-Chloro-4-(3-nitro-pyridin-2-ylamino)-phenyl]-acetic acid ethyl ester is obtained in the form of a solid. ES-MS: 336.0 [M+H]+; single peak at tR=5.59 min (System 1); Rf=0.39 (Hexane/EtOAc, 7:3).