[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[C:12]1([CH3:20])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Mg]Cl.[NH4+].[Cl-].[O-][Mn](=O)(=O)=O.[K+]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH3:20])[C:5]([C:6]([NH:8][CH3:9])=[O:7])=[CH:4][N:3]=1
A solution of 1.5 g (8.8 mmol) 6-chloro-N-methyl-nicotinamide in 18 ml THF was added at 4° C. over 15 min to a solution of 21.9 ml (21.9 mmol) o-tolylmagnesium chloride 1M in THF. The reaction mixture was stirred at r.t. for 2 h cooled to 4° C. and treated dropwise over 10 min with 30.0 ml 5% aqueous NH4Cl. The aqueous phase was separated and extracted twice with THF and the organic phases were washed twice with 5% aqueous NH4Cl. The combined organic phases were dried over Na2SO4 and subsequently treated at r.t. in four portions over 10 h with 0.9 g (5.7 mmol) KMnO4. The reaction mixture was stirred for 5.5 h at r.t., filtrated and the solvent was removed. The residue was purified by chromatography over silica gel (CHCl3) to yield 1.8 g (78.9%) product as a yellow oil.
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