反应详情

温度

75 °C

2-Chloro-5-fluoro-4-methyl-3-nitro-benzoic acid methyl ester (Preparation 1d, 53 g), 5% Pd/C (9 g) and ammonium formate (80 g) were stirred together in ethanol (500 mL) at 75° C. for 32 h. The reaction was filtered through celite and filtrate evaporated to a solid. This solid residue was dissolved in dichloromethane, washed with water. The separated aqueous layer was further extracted with dichloromethane (3×100 mL) and the combined organics dried (MgSO4) and evaporated. Analysis showed significant unreacted starting material. The reaction was repeated by new 5% P/C (9 g) and ammonium formate (80 g) together in ethanol (500 mL) and heating at 75° C. for 20 h. Further 5% Pd/C (9 g) and ammonium formate (80 g) were added and heating continued for 10 h. The mixture was filtered through celite and the filter cake was washed with further ethanol. The combined filtrates were evaporated, the residue dissolved in dichloromethane, washed with water. The separated aqueous layer was further extracted with dichloromethane (3×100 mL) and the combined organics dried (MgSO4) and evaporated to afford the subtitle compound (34.7 g).

1. filtrationThe reaction was filtered through celite and filtrate
2. customevaporated to a solid
3. dissolutionThis solid residue was dissolved in dichloromethane
4. washwashed with water
5. extractionThe separated aqueous layer was further extracted with dichloromethane (3×100 mL)
6. dry with materialthe combined organics dried (MgSO4)
7. customevaporated
8. additionFurther 5% Pd/C (9 g) and ammonium formate (80 g) were added
9. temperatureheating
10. filtrationThe mixture was filtered through celite
11. washthe filter cake was washed with further ethanol
12. customThe combined filtrates were evaporated
13. dissolutionthe residue dissolved in dichloromethane
14. washwashed with water
15. extractionThe separated aqueous layer was further extracted with dichloromethane (3×100 mL)
16. dry with materialthe combined organics dried (MgSO4)
17. customevaporated