반응 #4388

반응 방정식

sodium bicarbonate

2,3-diaminopyridine

2-methylbenzaldehyde

Sodium cyanoborohydride

→

2-amino-3-(2-methylbenzylamino)pyridine

수율 34.4%

용매

methanol

acetic acid

반응 조건

후처리

1. 1
   workup.STIRRINGwith stirring under ice-
2. 2
   온도cooling over a period of 20 minutes
3. 3
   workup.STIRRINGAfter being stirred for 3 hours
4. 4
   여과filtered by suction
5. 5
   기타The filtrate was evaporated in vacuo
6. 6
   workup.ADDITIONto the residue was added water
7. 7
   추출extracted with methylene chloride
8. 8
   세척The extract was washed with brine
9. 9
   건조dried over magnesium sulfate
10. 10
    기타evaporated in vacuo
11. 11
    기타The crystalline residue was recrystallized from a mixture of ethyl acetate and n-hexane

실험 절차

Molecular Sieves (16 g) was added to a solution of 2,3-diaminopyridine (8 g), 2-methylbenzaldehyde (8.81 g), and acetic acid (4.2 ml) in methanol (160 ml) and the mixture was stirred for 96 hours at room temperature. Sodium cyanoborohydride (4.61 g) was added portionwise to the mixture with stirring under ice-cooling over a period of 20 minutes. After being stirred for 3 hours, the mixture was made alkaline with aqueous sodium bicarbonate solution and filtered by suction. The filtrate was evaporated in vacuo, and to the residue was added water and then extracted with methylene chloride. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 2-amino-3-(2-methylbenzylamino)pyridine (5.38 g).

출처