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

HRID 2199250Notes

Reaction equation

HRID 2199250 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 86.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

In 20 ml of dimethylformamide, 3.00 g (18.6 mmol) of 2-chloro-5-chloromethylpyridine was dissolved, and 1.75 g (18.6 mmol) of 2-aminopyridine was added thereto, followed by stirring at 80° C. for 8 hours, and at room temperature for 5 hours. After completion of the reaction, dimethylformamide was distilled off under reduced pressure, and acetonitrile was added. As a result, a solid was precipitated. The solid was collected by filtration, thoroughly washed with acetonitrile, and then dried. Thus, 2.07 g of 1-[(6-chloropyridin-3-yl)methyl]pyridine-2(1H)-imine hydrochloride was obtained (Percentage Yield: 44%).

Workup

  1. waitat room temperature for 5 hours
  2. distillationwas distilled off under reduced pressure, and acetonitrile
  3. additionwas added
  4. customAs a result, a solid was precipitated
  5. filtrationThe solid was collected by filtration
  6. washthoroughly washed with acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-aeae018556a3468c8b3f0e5df19b684f
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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