Réaction #40402

Équation de réaction

5-chloroisatoic anhydride

2-amino-5-chloropyridine

potassium bis(trimethylsilyl)amide

toluene

→

(2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide

Rendement 100.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autredropwise at −78° C
2. 2
   TempératureThe mixture was warmed up
3. 3
   workup.STIRRINGstirred overnight
4. 4
   AutreAfter quenched by saturated ammonium chloride solution
5. 5
   Extractionthe mixture was extracted by ethyl acetate
6. 6
   SéchageThe organic layer was dried over magnesium sulfate
7. 7
   Concentrationconcentrated

Mode opératoire

To a solution of 2-amino-5-chloropyridine (328 mg, 2.55 mmol) in tetrahydrofuran (5 ml) was 0.5M potassium bis(trimethylsilyl)amide in toluene (10 ml, 5.05 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (0.5 g, 2.55 mmol) at −78° C. The mixture was warmed up to r.t gradually and stirred overnight. After quenched by saturated ammonium chloride solution, the mixture was extracted by ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to give (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide (0.71 g, 100%). MS found for C12H9Cl2N3O M+=282, (M+2)+=284.

Source