O-Phenylenediamine → 6-Chloro-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (2-amino-phenyl)amide

HRID 12282Notes

Reaction equation

HRID 12282 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[C:5](=[O:8])[NH:6][N:7]=1.[C:12]1([NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].Cl.C(N=C=NCCCN(C)C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:19][C:9]([C:4]1[C:5](=[O:8])[NH:6][N:7]=[C:2]([Cl:1])[CH:3]=1)=[O:11]

Participants

6

Reactant 3

HCID 7243O-PhenylenediamineHCID 3340156-Chloro-3-oxo-2,3-dihydropyridazine-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 866116096-Chloro-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (2-amino-phenyl)amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

30.5 g of 6-chloro-3-oxo-2,3-dihydropyridazine-4-carboxylic acid, 18 g of ortho-phenylenediamine and 2 g of DMAP are dissolved in 800 ml of DMF, at room temperature 32.2 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride are added, and the resulting solution is stirred at room temperature for 4 hours. For workup, the solvent is distilled off and the residue is suspended in water at 70° C. The precipitate is filtered off, washed several times with water and then dried in vacuo.

Workup

  1. additionare added
  2. distillationFor workup, the solvent is distilled off
  3. customis suspended in water at 70° C
  4. filtrationThe precipitate is filtered off
  5. washwashed several times with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9feb74f319eb4940b9784589c395aa8d
Source dataset
uspto-grants-2010_06
Patent number
US07727989B2

Reaction notes

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