Water → 2-Methoxy-8-nitroquinoline

HRID 2306255Notes

Reaction equation

HRID 2306255 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[NH:12][C:11](=[O:14])[CH:10]=[CH:9]2)([O-:3])=[O:2].[C:15]([O-])([O-])=O.[Cs+].[Cs+].IC.O>CN(C=O)C>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 3465208-Nitroquinolin-2(1H)-one

Product 1

HCID 184336082-Methoxy-8-nitroquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1,2-dihydro-8-nitroquinolin-2-one, as described above in Step C, (2.55 g, 13.41 mmol) in DMF (80 mL) were added Cs2CO3 (13.11 g, 40.23 mmol) and iodomethane (1.37 mL, 14.75 mmol) and the mixture was stirred vigorously for 2.5 hours. The reaction mixture was poured into water at 0° C. and the solid was isolated by filtration. The resulting solid was dried in vacuo, to yield the above-titled compound.

Workup

  1. customthe solid was isolated by filtration
  2. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-073aa1f48b334f07b5673d77feb0e0e4
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

Loading…