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

HRID 4292

Reaction equation

HRID 4292 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8afe18d01bb54bda9ec3d89b8bd7890e
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

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