반응 #328865

반응 방정식

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

용매

acetic acid

DMF

반응 조건

후처리

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

실험 절차

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)

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