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

HRID 623300Notes

Reaction equation

HRID 623300 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=O)C>[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 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3.00 g (18.6 mmol) of 2-chloro-5-chloromethyl pyridine was dissolved in 20 ml of anhydrous DMF, 1.75 g (18.6 mmol) of 2-aminopyridine was added thereto, and the resulting mixture was stirred at 80° C. for 8 hours and at room temperature for 5 hours. After the reaction was completed, DMF was distilled off under reduced pressure, acetonitrile was added thereto to precipitate a solid, and the solid was collected, washed well with acetonitrile and then dried to obtain 2.07 g (yield 44%) of 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride.

Workup

  1. distillationDMF was distilled off under reduced pressure, acetonitrile
  2. additionwas added
  3. customto precipitate a solid
  4. customthe solid was collected
  5. washwashed well with acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-90bae05e2b3541eb987dc28d6e2c1646
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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