5-Chloro-8-hydroxyquinoline → HCID 54052186, compound

HRID 579712Notes

Reaction equation

HRID 579712 reaction equation
[OH-].[Na+].C(Cl)Cl.[CH:6]1[CH:15]=[N:14][C:13]2[C:8](=[C:9]([Cl:17])[CH:10]=[CH:11][C:12]=2[OH:16])[CH:7]=1.[CH2:18](Br)[CH:19]=[CH:20][CH3:21]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:17][C:9]1[CH:10]=[CH:11][C:12]([O:16][CH2:18][CH:19]=[CH:20][CH3:21])=[C:13]2[C:8]=1[CH:7]=[CH:6][CH:15]=[N:14]2

Participants

7

Reactant 4

HCID 28175-Chloro-8-hydroxyquinolineHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 1224142-Butene, 1-bromo-

Product 1

HCID 54052186HCID 54052186, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

3.6 g (0.09 mol) of NaOH pellets are dissolved in 300 ml of water, and 300 ml of methylene chloride are added; there are subsequently added 10.8 g (0.06 mol) of 5-chloro-8-oxyquinoline, 16.2 g of 2-butenyl bromide (0.12 mol) and 0.5 g of tetra-n-butylammonium bromide, and the mixture is stirred for 5 hours at room temperature. The organic layer is separated, and the aqueous layer is extracted twice with methylene chloride. The organic solvents are combined and concentrated by evaporation. The residue is taken up in water and methylene chloride; the organic layer is then extracted by shaking three times with 2N NaOH, separated, dried with Na2SO4 and concentrated by evaporation; crude yield 15.5 g.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted twice with methylene chloride
  3. concentrationconcentrated by evaporation
  4. extractionthe organic layer is then extracted
  5. stirringby shaking three times with 2N NaOH
  6. customseparated
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2f8ca7da66144b28933c2cb15a05564b
Source dataset
uspto-grants-1988_06
Patent number
US04749406

Reaction notes

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