تفاعل #214384

معادلة التفاعل

2-methoxy-4-cyanopyridine

semicarbazide hydrochloride

sodium acetate

ethanol

→

2-methoxypyridine-4-carboxaldehyde

المردود 35.1%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was evaporated to a volume of 450 ml, water (900 ml)
2. 2
   workup.ADDITIONwas added
3. 3
   ترشيحThe mixture was filtered
4. 4
   غسيلthe solid was washed with water
5. 5
   workup.DISSOLUTIONwas dissolved in 10% hydrochloric acid (950 ml)
6. 6
   workup.ADDITIONFormaldehyde solution (36% w/v, 420 ml) was added
7. 7
   درجة الحرارةthe mixture was warmed for 30 minutes
8. 8
   درجة الحرارةto cool
9. 9
   workup.ADDITIONwas added to a solution of sodium acetate (280 g) in water (840 ml)
10. 10
    استخلاصThe mixture was extracted with ether (3×500 ml)
11. 11
    غسيلthe combined extracts were successively washed with aqueous potassium carbonate and water
12. 12
    أخرىwere dried out
13. 13
    أخرىevaporated

الإجراء التجريبي

A mixture of 2-methoxy-4-cyanopyridine (57.2 g), semicarbazide hydrochloride (71.24 g), sodium acetate (69.86 g), ethanol (1,200 ml) and water (370 ml) was hydrogenated at 344 kPa using Raney nickel catalyst (1.0 g). The mixture was evaporated to a volume of 450 ml, water (900 ml) was added and the mixture was allowed to stand at 0° overnight. The mixture was filtered and the solid was washed with water and was dissolved in 10% hydrochloric acid (950 ml). Formaldehyde solution (36% w/v, 420 ml) was added and the mixture was warmed for 30 minutes, allowed to cool and was added to a solution of sodium acetate (280 g) in water (840 ml). The mixture was extracted with ether (3×500 ml) and the combined extracts were successively washed with aqueous potassium carbonate and water and were dried out evaporated to give 2-methoxypyridine-4-carboxaldehyde (20.53 g, 35%) m.p. 33-5° . A sample recrystallised from petroleum ether had m.p. 33-36°.

المصدر