Toluene → 2-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide
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
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 C12H9Cl2N30 M+=282, (M+2)+=284.
Workup
- temperatureThe mixture was warmed up
- stirringstirred overnight
- concentrationAfter concentrated
- washthe crude was washed with saturated ammonium chloride solution
- extractionextracted by ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-42bf7a59ffb94eaa8381c69da71c088a
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518977B2
Reaction notes
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