[Cl-].[C:2]([CH2:5][N+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])(O)=O.[C:13](#[N:16])[CH:14]=C.CCN(CC)CC>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:12][C:7]1[N:6]2[C:11]([CH:10]=[CH:9][CH:8]=1)=[C:14]([C:13]#[N:16])[CH:2]=[CH:5]2To a solution of crude 1-Carboxymethyl-2-methyl-pyridinium chloride (7 g, 0.037 mol) in toluene (50 mL) were added acrylonitrile (7.4 mL, 0.11 mol), MnO2 (6.5 g, 0.075 mol) and Et3N (2 mL) at room temperature under nitrogen atmosphere. The solution was heated to 90 C and was stirred at the same temperature for 12 hours. The solution was cooled down and was filtered to remove the excess MnO2. The filtrate was concentrated and the residue was purified by CombiFlash with 10% EtOAc in Hexane to afford the desirable product 5-Methyl-indolizine-1-carbonitrile, CAS: 5-Methyl-indolizine-1-carbonitrile (3 g, 52%) as a white solid.
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