Chlorosuccinimide → HCID 86710116, compound

HRID 1468296Notes

Reaction equation

HRID 1468296 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:13])[CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:14]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([CH3:13])[C:5]([Cl:14])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 67440146HCID 67440146, compound

Product 1

HCID 86710116HCID 86710116, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 6-amino-2-methylisonicotinate (2.00 g, 11.1 mmol) was dissolved in DMF (20 mL), and the solution was stirred at 50° C. for 1 hour after adding N-chlorosuccinimide (1.48 g, 11.1 mmol). The reaction mixture was allowed to cool to room temperature, and a sodium hydrogen carbonate aqueous solution was added. The precipitated solid was collected by filteration to give ethyl 6-amino-3-chloro-2-methylisonicotinate (1.36 g, yield 57%).

Workup

  1. temperatureto cool to room temperature
  2. customThe precipitated solid was collected by filteration

Sources & evidence

ORD record
ord-55726e5ba6ad4077a18b613398b59b7a
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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