N-methyl-2-pyrrolidone → 7-Methyl-2-oxo-1,2-dihydroquinoline-6-carbonitrile

HRID 1465735Notes

Reaction equation

HRID 1465735 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]=[CH:7][CH:6]=[CH:5]2.CN1CCCC1=[O:19].[C:20]([Cu])#[N:21]>O>[CH3:12][C:11]1[CH:10]=[C:9]2[C:4]([CH:5]=[CH:6][C:7](=[O:19])[NH:8]2)=[CH:3][C:2]=1[C:20]#[N:21]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 579110186-Bromo-7-methylquinolineHCID 178418546HCID 178418546, compound

Product 1

HCID 916190707-Methyl-2-oxo-1,2-dihydroquinoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 6-bromo-7-methylquinolin (10 g, 42.0 mmol, prepared following J. Med. Chem. 1988, 31, 2048.), N-methyl-2-pyrrolidinone (32 mL), and CuCN (11 g, 0.13 mol) was stirred at 20° C. overnight and then at reflux temperature (202° C.) for 7 h. The mixture was poured into water (250 mL) and filtered, and the solid was washed twice with water to furnish 7-Methyl-2-oxo-1,2-dihydroquinoline-6-carbonitrile.

Workup

  1. temperatureat reflux temperature (202° C.) for 7 h
  2. filtrationfiltered
  3. washthe solid was washed twice with water

Sources & evidence

ORD record
ord-a5f4fe8986354811a32590097edab413
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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