Allyl bromide → HCID 19592399, compound

HRID 613460Notes

Reaction equation

HRID 613460 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:15](Br)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.ClCCl>[CH2:17]([O:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 178526532HCID 178526532, compound

Product 1

HCID 19592399HCID 19592399, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-hydroxy-8-nitroquinoline (200 mg) and allyl bromide (140 mg) in dimethylformamide (2 ml) was added potassium carbonate (290 mg) at 0° C., and the mixture was stirred for 6 hours at 50° C. The mixture was diluted with dichloromethane and washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved into hot ethyl acetate (2 ml), and the solution was stirred at ambient temperature. The resulting precipitate was collected by filtration to give 4-allyloxy-8-nitroquinoline (120 mg).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved into hot ethyl acetate (2 ml)
  5. stirringthe solution was stirred at ambient temperature
  6. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-17a92ecdabb346b6853d2809f318d014
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…