4-Chloroaniline → 2-chloro-N-(4-chlorophenyl)pyridine-3-carboxamide

HRID 493228

Reaction equation

HRID 493228 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]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 5879062-chloro-N-(4-chlorophenyl)pyridine-3-carboxamideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. washthe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (100 mL) twice
  2. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off
  5. washThe solid was washed with diethyl ether:ethyl acetate (3:1)
  6. customdried under reduced pressure
  7. customto give 4.2 g of the title reference compound as a white solid

Sources & evidence

ORD record
ord-98e58577013940c08800b3b09368983f
Source dataset
uspto-grants-2009_05
Patent number
US07534802B2

Linked notes

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