Toluene → 2-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

HRID 2362794Notes

Reaction equation

HRID 2362794 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[Cl:26][C:27]1[CH:38]=[C:31]2[C:32](OC(=O)[NH:36][C:30]2=[CH:29][CH:28]=1)=[O:33]>O1CCCC1>[NH2:36][C:30]1[CH:29]=[CH:28][C:27]([Cl:26])=[CH:38][C:31]=1[C:32]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1)=[O:33]

Participants

6

Reactant 4

HCID 1140TolueneHCID 661742-Amino-5-chloropyridineHCID 784805-Chloroisatoic anhydrideHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-amino-5-chloropyridine (787 mg, 6.1 mmol) in tetrahydrofuran (5 ml) was added 0.5M potassium bis(trimethylsilyl)amide in toluene (20 ml, 10.1 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (1 g, 5.1 mmol) at −78° C. The mixture was warmed up to r.t gradually and stirred overnight. After concentrated, the crude was washed with saturated ammonium chloride solution and 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 as yellow solid (1.39 g. 99%). MS found for C12H9Cl2N3O M+=282, (M+2)+=284. Step 2:

Workup

  1. temperatureThe mixture was warmed up
  2. stirringstirred overnight
  3. concentrationAfter concentrated
  4. washthe crude was washed with saturated ammonium chloride solution
  5. extractionextracted by ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-766ee8cd8de44308982f1b714b53ca23
Source dataset
uspto-grants-2014_04
Patent number
US08691847B2

Reaction notes

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