2,3-Dichloroaniline → HCID 56162074, compound

HRID 1518510Notes

Reaction equation

HRID 1518510 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:10][C:11]1[CH:12]=[C:13]([C:18](Cl)=[O:19])[C:14]([Cl:17])=[N:15][CH:16]=1>C(OCC)C>[Br:10][C:11]1[CH:12]=[C:13]([C:18]([NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:2]=2[Cl:1])=[O:19])[C:14]([Cl:17])=[N:15][CH:16]=1

Participants

4

Reactant 2

HCID 118442,3-DichloroanilineHCID 126772955-Bromo-2-chloro-3-pyridinecarbonyl chloride

Product 1

HCID 56162074HCID 56162074, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2,3 dichloroaniline (3.875 g, 23.914 mmol) in diethyl ether (20 mL) was added 5-bromo-2-chloropyridine-3-carbonyl chloride (3.0 g, 11.96 mmol). The reaction was stirred overnight. The precipitated solids were collected and washed with diethyl ether to provide 3.6 g of 5-bromo-2-chloro-N-(2,3-dichlorophenyl)pyridine-3-carboxamide as a cream colored solid [LC-MS m/e=380.0 (M+H)]. Using the same procedure, 5-bromo-2-chloro-N-(2,3-fluorophenyl)pyridine-3-carboxamide and 5-bromo-2-chloro-N-(3-chloro-2-fluorophenyl)pyridine-3-carboxamide can be produced from reacting 5-bromo-2-chloropyridine-3-carbonyl chloride with 2,3 fluororoaniline and 3-chloro-2-fluoroaniline, respectively.

Workup

  1. customThe precipitated solids were collected
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-40f9b09da86e40459a35d151f827bf46
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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