Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14]([NH2:17])[CH:15]=[CH2:16]>CO>[N+:11]([C:3]1[CH:4]=[C:5]([C:8]([OH:10])=[O:9])[CH:6]=[N:7][C:2]=1[NH:17][CH2:14][CH:15]=[CH2:16])([O-:13])=[O:12]To a solution of 6-chloro-5-nitro-3-pyridinecarboxylic acid (4.72 g, 23.30 mmol) in methanol (70 mL) at room temperature was added allyl amine (5.25 mL, 70.0 mmol) and the mixture was stirred overnight. The reaction was then concentrated in vacuo and the residue taken up into water (100 mL). The solution was brought to pH 3 by addition of 1 M HCl aqueous solution. The resulting suspension was extracted with EtOAc (50 mL). The aqueous phase was back-extracted with additional EtOAc (2×50 mL). The organic phases were combined, dried with MgSO4, and filtered. The solution was concentrated in vacuo providing 5-nitro-6-(2-propenylamino)-3-pyridinecarboxylic acid which was used without further purification.
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