Propargyl bromide → HCID 22048511, compound

HRID 749063Notes

Reaction equation

HRID 749063 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[Cl:13])=[CH:10][C:9]([OH:14])=[C:8]([O:15][CH3:16])[CH:7]=2)#[N:2].[CH2:17](Br)[C:18]#[CH:19].[O-]CCCC.[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(N(C)C)=O>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[Cl:13])=[CH:10][C:9]([O:14][CH2:19][C:18]#[CH:17])=[C:8]([O:15][CH3:16])[CH:7]=2)#[N:2]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 22048520HCID 22048520, compoundHCID 23699084Potassium butoxide

Product 1

HCID 22048511HCID 22048511, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 31374DimethylacetamideSolvent

Procedure

The product from step 1 (1 g) was reacted with propargyl bromide (0.95 g) in the presence of potassium butoxide (0.53 g), tetrabutylammonium iodide (0.16 g) and 18C-6 crown ether (0.05 g), in solution in DMA (100 ml, 10° C. to ambient temperature). 3-cyano-4-chloro-6-propargyloxy-7-methoxyquinoline (0.73 g) was obtained.

Sources & evidence

ORD record
ord-f689e6296c9d46f2a3fafe17b3d9d3d2
Source dataset
uspto-grants-2008_07
Patent number
US07402583B2

Reaction notes

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