Реакция #1509581

Уравнение реакции

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

Растворители

acetic acid

DMF

Условия реакции

Обработка

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

Методика

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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