تفاعل #1509581

معادلة التفاعل

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

المذيبات

acetic acid

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)

المصدر