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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 641807Generated: October 25, 2026

Dimethylformamide → 6-Quinolinamine, N,N,2-trimethyl-

https://huagongshe.com/reaction/641807

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactant2-Methylquinolin-6-amineHCID 103148—
SolventWaterHCID 962—
Product6-Quinolinamine, N,N,2-trimethyl-HCID 66725—

Reaction Conditions

Temperature40 °C

Reaction Steps

A mixture of 2-methylquinolin-6-amine (2.4 g, 15.2 mmol) and NaH (2.4 g, 60.8 mmol) in DMF (60 mL) was stirred at 40° C. for 3 hrs. Then CH3I (3.8 mL, 60.8 mmol) was added by syringe. The reaction mixture was stirred at 40° C. overnight and then cooled to room temperature. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine and dried over anhydrous Na2SO4. After purified by column chromatography (hexane/EtOAc=25:1), compound 3 was obtained (1.1 g, 39%). MS [M++1]=187, LC-MS: tR=0.775 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07696227B2
Source datasetuspto-grants-2010_04
ORD IDord-27edef64dbe8400a8d9ddb00b5885a6f
Source noteuspto-grants-2010_04