4-Chloroaniline → 2-chloro-N-(4-chlorophenyl)pyridine-3-carboxamide
Reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[C:3]([C:4]([NH:16][C:15]2[CH:17]=[CH:18][C:12]([Cl:11])=[CH:13][CH:14]=2)=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1Participants
Procedure
2-Chloronicotinoyl chloride (4.0 g, 23 mmol) was added to a solution of 4-chloroaniline (3.2 g, 25 mmol) and N,N-diisopropylethylamine (7.7 mL, 46 mmol) in tetrahydrofuran (40 mL), and then the mixture was stirred at room temperature for 3 hours. Ethyl acetate (150 mL) was added to the reaction mixture, and the ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (100 mL) twice and brine (100 mL) twice. The ethyl acetate layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the precipitated solid was filtered off. The solid was washed with diethyl ether:ethyl acetate (3:1), and then dried under reduced pressure to give 4.2 g of the title reference compound as a white solid. (Yield 82%)
Workup
- washthe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (100 mL) twice
- dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- filtrationthe precipitated solid was filtered off
- washThe solid was washed with diethyl ether:ethyl acetate (3:1)
- customdried under reduced pressure
- customto give 4.2 g of the title reference compound as a white solid
Sources & evidence
- ORD record
- ord-43111298a846476ba8f75e073477ac9f
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518973B2
Reaction notes
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