(3,4-Dichlorophenyl)hydrazine monohydrochloride → 1-(3,4-Dichlorophenyl)-5-pyridin-3-yl-1H-pyrazole-3-carboxylic acid methyl ester hydrochloride

HRID 480100Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4](O)=[CH:5][C:6](=O)[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.Cl.[Cl:17][C:18]1[CH:19]=[C:20]([NH:25][NH2:26])[CH:21]=[CH:22][C:23]=1[Cl:24]>CCO>[ClH:17].[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:25]([C:20]2[CH:21]=[CH:22][C:23]([Cl:24])=[C:18]([Cl:17])[CH:19]=2)[N:26]=1)=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1 (2.90 g, 14.0 mmol) in EtOH (60 mL, anhydrous) was added 3,4-dichlorophenyl hydrazine hydrochloride (3.29 g, 15.4 mmol). The solution was heated to reflux for 30 min and then cooled to 0° C. The precipitate was collected by filtration and washed with H2O and MeOH to yield 2 (3.79 g, 70%) as an off-white powder.

Workup

temperatureThe solution was heated
temperatureto reflux for 30 min
filtrationThe precipitate was collected by filtration
washwashed with H2O and MeOH

Sources & evidence

ORD record: ord-e555c74ef3b844d98a6b303af6a60dff
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649638B1

Reaction notes

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