تفاعل #1874839

معادلة التفاعل

2-Methyl-7H-[1,7]naphthyridin-8-one

phosphorus oxychloride

→

desired compound

8-Chloro-2-methyl-[1,7]naphthyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was evaporated to dryness
2. 2
   workup.ADDITIONpoured on ice and set alkaline with aqueous ammonia
3. 3
   أخرىA red solution resulted
4. 4
   استخلاصThe aqueous layer was extracted with dichloromethane (three times)
5. 5
   غسيلThe combined organic layers were washed with brine
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe residue was purified by flash chromatography on silica gel (ethyl acetate/heptane 0:100->20:80 gradient)

الإجراء التجريبي

A suspension of 2-Methyl-7H-[1,7]naphthyridin-8-one (820 mg, 5.12 mmol) and phosphorus oxychloride (7 ml, 76.8 mmol) was stirred at 90° C. for 4 hours. The reaction mixture was evaporated to dryness, poured on ice and set alkaline with aqueous ammonia. A red solution resulted. The aqueous layer was extracted with dichloromethane (three times). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate/heptane 0:100->20:80 gradient). The desired compound was obtained as a white solid (810 mg, 89%), MS: m/e=(M+H+).

المصدر