Chlorosuccinimide → 2-Amino-5-chloro-isonicotinonitrile

HRID 1468288Notes

Reaction equation

HRID 1468288 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[Cl:10]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[C:5]([Cl:10])=[CH:4][N:3]=1.[NH2:1][C:2]1[C:7]([Cl:10])=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 70155242-Aminoisonicotinonitrile

Product 2

HCID 840711262-Amino-5-chloro-isonicotinonitrileYield 60%HCID 867100972-Amino-3-chloro-4-pyridinecarbonitrileYield 2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Amino-4-cyanopyridine (8.00 g, 67.2 mmol) was dissolved in DMF (40 mL), and the solution was stirred at 50° C. for 1 hour after adding N-chlorosuccinimide (8.97 g, 67.2 mmol). After the reaction was completed, a sodium hydrogen carbonate aqueous solution was added under ice-cooled condition, and the precipitated solid was collected by filteration. The resulting solid was purified by silica gel column chromatography (chloroform/methanol=95/5→90/10, heptane/ethyl acetate=65/35→50/50) to give 2-amino-5-chloro-4-cyanopyridine (6.23 g, yield 60%) and 2-amino-3-chloro-4-cyanopyridine (0.254 g, yield 2%).

Workup

  1. temperaturecooled condition
  2. customthe precipitated solid was collected by filteration
  3. customThe resulting solid was purified by silica gel column chromatography (chloroform/methanol=95/5→90/10, heptane/ethyl acetate=65/35→50/50)

Sources & evidence

ORD record
ord-cd856b6d9f2d425496a251286cd924b5
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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