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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 445539Generated: October 25, 2026

Hydrochloric Acid → (6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amine

https://huagongshe.com/reaction/445539

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantPempidineHCID 6603—
Reactant1,3-dimethyl-1H-pyrazol-4-amineHCID 4431056—
Reactant6-Bromo-4-chloro-3-nitroquinolineHCID 21984128—
SolventDimethylacetamideHCID 31374—
Product(6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amineHCID 59619997—

Reaction Conditions

Temperature50 °C

Reaction Steps

To a mixture of 6-bromo-4-chloro-3-nitro-quinoline (Stage A.4, 3.0 g, 20.43 mmol) and 4-amino-1,3-dimethylpyrazole.HCl (ChemCollect, Remscheid, Germany, 1.85 g, 12.53 mmol) in DMA (45 ml) was added 1,2,2,6,6-pentamethylpiperidine (6.67 ml, 36.5 mmol). The RM was stirred at 50° C. for 4.5 h. Then the RM was cooled down to rt and quenched with H2O. The suspension was filtered, the solid cake was washed with H2O and dried under vacuum, before being dissolved in EtOAc. The solution was washed with brine (2×), dried over Na2SO4, filtered and evaporated to dryness to give the title compound as an orange solid (HPLC tR 2.55 min (Method A); M+H=362; M−H=360 MS-ES)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08476294B2
Source datasetuspto-grants-2013_07
ORD IDord-107e0d394ec241819ab4fdd628a3d338
Source noteuspto-grants-2013_07