Sodium Carbonate → 3-Nitroquinoline

HRID 1938333Notes

Reaction equation

HRID 1938333 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9](O)[CH:8]=2)([O-:3])=[O:2].[H-].[Na+].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(N(CC)CC)C.CS(C)=O.O1CCCC1.N1C=CC=CC=1.ClCCl.C1(C)C=CC=CC=1.C1C=CC=CC=1.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]

Participants

13

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 1357342933-Nitroquinolin-7-ol

Product 1

HCID 255513-Nitroquinoline

Reagents, catalysts & solvents 8

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

The 3-nitro-7-hydroxyquinoline of the formula (a) is reacted with a halogenated compound of the formula (b) in an inert solvent such as dimethylformamide (DMF), benzene, toluene, dichloromethane, pyridine, tetrahydrofuran (THF), or dimethylsulfoxide (DMSO) in the presence of a base such as sodium hydride, sodium alkoxide, triethylamine, sodium hydroxide, or sodium carbonate, to give the 3-nitroquinoline derivative of the formula (c).

Sources & evidence

ORD record
ord-12fba08e6fc3489fb9ff77c07c1d6db2
Source dataset
uspto-grants-1997_12
Patent number
US05693651

Reaction notes

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