[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1C(O)=O.[N-:12]=[N+]=[N-].[Na+].O>O=S(Cl)Cl>[CH3:1][C:2]1[C:3]([NH2:12])=[C:7]([CH3:11])[CH:8]=[CH:9][N:10]=12,4-dimethylnicotinic acid (3.0 g, 20 mmol) was added in SOCl2 (20 mL) at 0° C. and warmed to 60° C. After stirring for 1 hr, the reaction was concentrated under vacuum. The residue was dissolved in acetone (20 mL) and NaN3 (1.9 g, 30 mmol) followed by H2O (20 mL). The reaction was warmed to 70° C. and stirred for 1 hr at the same temperature. The reaction was cooled to room temperature and concentrated under vacuum to a half volume and poured into H2O (50 mL) and extracted with ethyl acetate (50 mL×5) and dried over MgSO4. The ethyl acetate was concentrated under vacuum to afford the crude compound. The compound was used for the next step without further purification. 1HNMR (CDCl3, 400 MHz) δ 2.10 (s, 3H), 2.30 (s, 3H), 4.65-4.70 (b, 2H), 6.85 (d, J=4.78 Hz, 1H), 7.75 (d, J=4.78 Hz, 1H). Exact mass calculated for C7H10N2 122.08. found 123.1 (MH+).
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