反応 #1509581

反応方程式

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

溶媒

acetic acid

DMF

反応条件

後処理

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
   その他The solvent was removed under reduced pressure
5. 5
   その他the residue partitioned between saturated aqueous solution of NaHCO3 and EtOAc
6. 6
   その他The organic phase was separated
7. 7
   洗浄washed with brine
8. 8
   その他dried under Na2SO4
9. 9
   ろ過filtered
10. 10
    その他the solvent was evaporated under reduced pressure
11. 11
    その他The crude was purified by flash column chromatography (10 g Isolute® silica gel cartridge; gradient elution: hexane/EtOAc from 1/1 to 3/7)

実験手順

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)

出典