2,4-Dichloroaniline → N-(2,4-dichlorophenyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide

HRID 970173Notes

Reaction equation

HRID 970173 reaction equation
ClC1C=C(Cl)C=CC=1CNC(C1C(=O)NN=C(C2C=CN=CC=2)C=1)=O.[O:26]=[C:27]1[C:32]([C:33]([OH:35])=O)=[CH:31][C:30]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)=[N:29][NH:28]1.C(Cl)(=O)C(Cl)=O.[Cl:48][C:49]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:50]=1[NH2:51]>C(N(CC)CC)C.CN(C)C=O.ClCCl>[Cl:48][C:49]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:50]=1[NH:51][C:33]([C:32]1[C:27](=[O:26])[NH:28][N:29]=[C:30]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)[CH:31]=1)=[O:35]

Participants

8

Reactant 4

HCID 111232,4-DichloroanilineHCID 65578Oxalyl chlorideHCID 10339420N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamideHCID 127902383-Oxo-6-(pyridin-4-yl)-2,3-dihydropyridazine-4-carboxylic acid

Product 1

HCID 10473713N-(2,4-dichlorophenyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamideYield 199.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Working as in example 2 for the preparation of N-(2,4-dichlorobenzyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide, but starting with 0.3 g of 3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxylic acid, 10 cm3 of dichloromethane, 0.02 cm3 of dimethylformamide, 0.12 cm3 of oxalyl chloride, 0.036 g of 2,4-dichloroaniline and 0.19 cm3 of triethylamine, 0.16 g of N-(2,4-dichlorophenyl)-3-oxo-6-pyridin-4-yl-2,3-dihydropyridazine-4-carboxamide was obtained in the form of a cream-colored solid melting above 260° C.

Sources & evidence

ORD record
ord-a8c80f213ead46948498895ca62483bf
Source dataset
uspto-grants-2007_12
Patent number
US07309701B2

Reaction notes

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