Chlorosuccinimide → 5-Chloro-3-methoxypyridin-2-amine

3-Methoxy-2-aminopyridine (Wonda Science, cat #01683; 12.4 g, 0.01 mol) is dissolved by stirring in 500 ml of ethyl acetate. A thermometer is placed in the solution to monitor temperature. N-Chlorosuccinimide (13.3 g, 0.01 mol) is added in several portions to keep the solution at room temperature. The solution becomes dark in color and is stirred at room temperature overnight. The supernatant is decanted from the dark solids that formed and transferred to a separatory funnel. The organic solution is washed with 500 ml saturated aqueous sodium bisulfite and then 500 ml brine. The organic layer is dried with MgSO4 and concentrated on a rotovap. The dark brown crude product is chromatographed on 500 g of flash silica-gel eluting with 30% EtOAc/Hexanes. Concentration of the appropriate fractions on a rotovap gives a yellow solid. The solid is suspended in hexanes, stirred and filtered to give the product as a bright yellow solid. (MP 93-94° C.).

1. customat room temperature
2. customThe supernatant is decanted from the dark solids
3. customthat formed
4. customtransferred to a separatory funnel
5. washThe organic solution is washed with 500 ml saturated aqueous sodium bisulfite
6. dry with materialThe organic layer is dried with MgSO4
7. concentrationconcentrated on a rotovap
8. customThe dark brown crude product is chromatographed on 500 g of flash silica-gel
9. washeluting with 30% EtOAc/Hexanes
10. customConcentration of the appropriate fractions on a rotovap gives a yellow solid
11. stirringstirred
12. filtrationfiltered

ORDレコード

ord-c33a7559a6b2488da063d38bd8bd84ef

出典データセット

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08618302B2