2-Aminopyridine → 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride

HRID 520746Notes

Reaction equation

HRID 520746 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][N:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]2=[NH:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 866869301-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochlorideYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

2-chloro-5-chloromethylpyridine in an amount of 3.00 g (18.6 mmol) was dissolved in 20 mL of anhydrous dimethylformamide (DMF), 1.75 g (18.6 mmol) of 2-aminopyridine was added, and the mixture was stirred out at 80° C. for 8 hours and at room temperature for 5 hours. Following reaction completion, DMF was distilled off under reduced pressure and acetonitrile was added, whereupon a solid separated out. The solid was collected by filtration, thoroughly washed with acetonitrile, then dried, giving 2.07 g of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride (yield, 44%).

Workup

  1. distillationwas distilled off under reduced pressure and acetonitrile
  2. additionwas added, whereupon a solid
  3. customseparated out
  4. filtrationThe solid was collected by filtration
  5. washthoroughly washed with acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-d8c14ff9c37146afa8b0894895954b08
Source dataset
uspto-grants-2016_05
Patent number
US09328068B2

Reaction notes

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