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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2116780Generated: October 31, 2026

Acetic Acid → 2-Bromo-3-(but-2-ynyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one

https://huagongshe.com/reaction/2116780

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantHydrazine hydrate (1:1)HCID 24654—
Reactantethyl 2-bromo-3-(but-2-ynyl)-5-formyl-3H-imidazole-4-carboxylateHCID 11522264—
SolventEthanolHCID 702—
Product2-Bromo-3-(but-2-ynyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-oneHCID 21947658—

Reaction Conditions

Temperature100 °C

Reaction Steps

6.31 ml (0.126 mol) hydrazine hydrate were added drop-wise at ambient temperature to a solution of 35.0 g (0.117 mol) ethyl 2-bromo-3-(but-2-ynyl)-5-formyl-3H-imidazole-4-carboxylate in 400 ml of ethanol. After 30 min stirring 27 ml (0.472 mol) concentrated acetic acid were added and the solution was then stirred for 1 h at 100° C. After cooling the precipitated solid was suction filtered, washed with ethanol and diethyl ether and dried. The solid was further purified by re-crystallization from EtOH.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07439370B2
Source datasetuspto-grants-2008_10
ORD IDord-bdaf642b29db445d96c4e066103cd9b6
Source noteuspto-grants-2008_10