2,3-Diaminopyridine → 2-Amino-3-(2-methylbenzylamino)pyridine

HRID 4292

반응식

HRID 4292 반응식
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[NH2:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 99562,3-DiaminopyridineHCID 107222-MethylbenzaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 138258912-Amino-3-(2-methylbenzylamino)pyridine수율 34.4%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

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).

후처리

  1. stirringwith stirring under ice-
  2. temperaturecooling over a period of 20 minutes
  3. stirringAfter being stirred for 3 hours
  4. filtrationfiltered by suction
  5. customThe filtrate was evaporated in vacuo
  6. additionto the residue was added water
  7. extractionextracted with methylene chloride
  8. washThe extract was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe crystalline residue was recrystallized from a mixture of ethyl acetate and n-hexane

출처 및 근거

ORD 기록
ord-8afe18d01bb54bda9ec3d89b8bd7890e
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725601

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