[CH2:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=1C1C=CC=CC=1)[CH2:2][CH3:3].ClCCl.CN(C)C(Cl)=O.[C:26](=O)([O-:28])[O-:27].[K+].[K+]>Cl>[CH2:1]([C:4]1[CH:5]=[CH:6][N:7]=[C:8]([C:26]([OH:28])=[O:27])[CH:9]=1)[CH2:2][CH3:3]To 4-propyl-(3-phenyl)pyridine-N-Oxide (1 g, 4.69 mmol) in dichloromethane (10 mL) trimethylsilyl cyanide (1.3 mL, 10 mmol) and dimethylcarbamyl chloride (1 mL, 10 mmol) was added and stirred at room temperature for 24 hours. Aqueous potassium carbonate (10%, 10 mL) was added and extracted with dichloromethane (100 mL). The crude product obtained on removal of solvent was taken in hydrochloric acid (6N, 30 mL) and refluxed for 24 hours. Removal of acid followed by crystallization of the crude product from acetonitrile resulted in acid 10b (1 g, 86%): MS (EPOS): 240 [M−1]; 1H NMR (300 MHz, CD3OD) δ 2.03–2.17 (m, 2), 2.74 (t, J=7.2, 2), 3.04 (t, J=7.8, 2), 7.16–7.38 (m, 5), 8.07 (d, J=4.2, 1), 8.40 (s, 1), 8.71 (d, J=5.7, 1).
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