[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][N:7]=1.CCO[C:18]([CH3:20])=O.[OH-].[Na+]>C1C=CC=CC=1>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](=[O:11])[C:20]2[CH:18]=[CH:14][CH:13]=[CH:9][CH:8]=2)=[CH:8][N:7]=1Aluminum chloride (100 g, 0.730 mol) was suspended in 200 ml benzene under N2. A solution of 6-chloronicotinoyl chloride (53 g, 0.30 mol) in 100 ml benzene was added to the rapidly stirring suspension then refluxed overnight. The reaction was cooled to RT, 1 L EtOAc was added, and the pH was adjusted to 8.5 with 5N NaOH. Aluminum salts precipitated and were filtered away. The filtrate was washed with H2O, dried over Na2SO4, and concentrated in vacuo. The resulting tan solid was recrystallized from 3:2 Et2O:hexanes yielding 54.6 g (83%) of product as tan crystals. EA, MS(FD).
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