反应详情

温度

75 °C

A mixture of 5-methyl-nicotinic acid (1.8 g, 13.1 mmole) and SOCl2 (10 mL) was heated to 75° C. for three hours. The remaining SOCl2 was removed by vacuum distillation and the oily residue carefully redissolved in dichloromethane (16 mL). Then N,O-dimethylhydroxyl amine hydrochloride (1.4 g, 14.4 mmol) was added. The reaction mixture was purged with argon and triethylamine (5.11 mL, 36.7 mmol) was dropwise added at 0° C. It was stirred for 24 hours at room temperature. The mixture was diluted with dichloromethane, washed with NaOH 2N, brine, dried and concentrated to yield a brown oil which was purified by column chromatography (SiO2, n-Hex/EtOAc 1:1 to EtOAc) to afford the title compound (1.7 g, 71% yield) as a brownish oil.

1. customThe remaining SOCl2 was removed by vacuum distillation
2. dissolutionthe oily residue carefully redissolved in dichloromethane (16 mL)
3. additionwas dropwise added at 0° C
4. washwashed with NaOH 2N, brine
5. customdried
6. concentrationconcentrated
7. customto yield a brown oil which
8. customwas purified by column chromatography (SiO2, n-Hex/EtOAc 1:1 to EtOAc)