反应 #1509581

反应方程式

hydrazine acetate

2-Chloro-6-methyl-isonicotinamide

N,N-dimethylformamide dimethyl acetal

→

2-Chloro-6-methyl-4-(1H-[1,2,4]triazol-3-yl)-pyridine

溶剂

acetic acid

DMF

反应条件

后处理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   温度The mixture was heated to 90° C.
3. 3
   workup.STIRRINGstirred for 1 h
4. 4
   其他The solvent was removed under reduced pressure
5. 5
   其他the residue partitioned between saturated aqueous solution of NaHCO3 and EtOAc
6. 6
   其他The organic phase was separated
7. 7
   洗涤washed with brine
8. 8
   其他dried under Na2SO4
9. 9
   过滤filtered
10. 10
    其他the solvent was evaporated under reduced pressure
11. 11
    其他The crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 1/1 to 3/7)

实验过程

2-Chloro-6-methyl-isonicotinamide (1.23 g) and N,N-dimethylformamide dimethyl acetal (1.05 ml) were dissolved in dry DMF (4 ml) under inert atmosphere and the resulting solution was heated to 90° C. and stirred for 1 h. The reaction mixture was cooled to room temperature and a solution of hydrazine acetate (3.32 g) in acetic acid (8 ml) was dropwise added. The mixture was heated to 90° C. and stirred for 1 h. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous solution of NaHCO3 and EtOAc. The organic phase was separated, washed with brine, dried under Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 1/1 to 3/7) affording 2-Chloro-6-methyl-4-(1H-[1,2,4]triazol-3-yl)-pyridine (0.92 g). GC (Rt)=13.21 min (method=3A)

来源