1,2-Dichloroethane → 2-chloro-N-(4-chlorophenyl)pyridine-3-carboxamide

HRID 2109601Notes

Reaction equation

HRID 2109601 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CCN(C(C)C)C(C)C.[CH2:20]([Cl:23])[CH2:21]Cl.C1C=[CH:26][C:27]2N(O)N=[N:30][C:28]=2[CH:29]=1>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:4]([NH:30][C:28]2[CH:29]=[CH:21][C:20]([Cl:23])=[CH:26][CH:27]=2)=[O:6])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 762582-Chloronicotinic acidHCID 81531Diisopropylethylamine

Product 1

HCID 5879062-chloro-N-(4-chlorophenyl)pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-chloronicotinic acid (4 g) and 4-chloroanaline (3.2 g) and DIEA (6 ml) in CH2Cl2 (200 ml) was added EDC (6 g) and HOBt (3.3 g). The reaction was stirred at RT overnight and washed with 2 N NaOH (100 ml), H2O (150 ml) and brine (100 ml). The organic layer was dried over Na2SO4 and evaporated to give (2-chloro(3-pyridyl))-N-(4-chlorophenyl)carboxamide.

Workup

  1. washwashed with 2 N NaOH (100 ml), H2O (150 ml) and brine (100 ml)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-e9a9a894afd741538cd68a6c94b432ff
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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