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Hydrochloric Acid → 6-chloro-N'-{6-[methyl(phenyl)amino]pyridazin-3-yl}pyridine-2-carbohydrazide

HRID 346511
Notes
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Reaction equation

HRID 346511 reaction equation
[NH:1]([C:3]1[N:8]=[N:7][C:6]([N:9]([CH3:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)[NH2:2].[Cl:17][C:18]1[N:23]=[C:22]([C:24](O)=[O:25])[CH:21]=[CH:20][CH:19]=1.Cl>C(Cl)Cl>[Cl:17][C:18]1[N:23]=[C:22]([C:24]([NH:2][NH:1][C:3]2[N:8]=[N:7][C:6]([N:9]([CH3:16])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:5][CH:4]=2)=[O:25])[CH:21]=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 208126-Chloropicolinic acidHCID 210818446-hydrazino-N-methyl-N-phenylpyridazine-3-amine

Product 1

HCID 210818436-chloro-N'-{6-[methyl(phenyl)amino]pyridazin-3-yl}pyridine-2-carbohydrazideYield 30.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydrazino-N-methyl-N-phenylpyridazine-3-amine (1.14 g) in methylene chloride (10 ml), 6-chloropicolic acid (0.83 g) and WSCD hydrochloride (1.22 g) were added, and the mixture was stirred at room temperature overnight. The reaction solution was purified by silica gel column chromatography (eluent: chloroform) to obtain 6-chloro-N′-{6-[methyl(phenyl)amino]pyridazin-3-yl}pyridine-2-carbohydrazide (0.57 g). This compound (0.56 g) was stirred at 150° C. overnight in xylene (20 ml), and the reaction solution was concentrated to obtain 3-(chloropyridin-2-yl)-N-methyl-N-phenyl-1,2,4-triazolo[4,3-b]pyridazine-6-amine (0.54 g) as colorless solids.

Workup

  1. customThe reaction solution was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-0d15d04f87134a0ea1bdf49eb3d5b4f2
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07173033B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes