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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 613281Generated: October 28, 2026

Dimethyl Sulfoxide → 1,3-dimethyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

https://huagongshe.com/reaction/613281

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
ReactantBenzylamineHCID 7504—
Reactant4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]quinolineHCID 13448999—
SolventWaterHCID 962—
Product1,3-dimethyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineHCID 19592228—

Reaction Conditions

Temperature85 °C

Reaction Steps

A mixture of 1,3-dimethyl-4-chloro-1H-pyrazolo[3,4-b] quinoline (1.2 g, 0.005 mol), benzylamine (1.2 ml) and DMSO (3 ml) was heated at 80-90° C. for 3-4 hours. The reaction mixture was cooled to room temperature and then was poured into water. The mixture was extracted with CH2Cl2 (3×50 ml) and then the CH2Cl2 layers were combined and evaporated. The residue was purified by column chromatography on silca gel eluting with ethyl acetate to afford the product which was crystallized from ether/hexane to afford 1.2 g of 1,3-dimethyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid, m.p. 105° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06008226
Source datasetuspto-grants-1999_12
ORD IDord-2502e3c8515b436b8e5c421ff22c759c
Source noteuspto-grants-1999_12