Dabco → HCID 69518032, compound

HRID 1831321Notes

Reaction equation

HRID 1831321 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH3:12][N:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14](Cl)=[O:15].N12CCN(CC1)CC2>ClCCl>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][C:14](=[O:15])[N:13]([CH3:12])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 113746-HydroxyquinolineHCID 77969Carbamic chloride, N-methyl-N-phenyl-

Product 1

HCID 69518032HCID 69518032, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-hydroxyquinoline (1.00 g, 6.89 mmol), N-methyl-N-phenylcarbamoyl chloride (1.17 g, 6.89 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.77 g, 6.89 mmol) in dichloromethane (20 mL) was stirred at room temperature for 1.25 hours. More dichloromethane was added and the solution was extracted with water. The organic layer was dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50). Evaporation of the solvent and recrystallised from ethylacetate/heptane yielded the title compound (1.33 g, 69% yield) as a white solid.

Workup

  1. extractionthe solution was extracted with water
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50)
  6. customEvaporation of the solvent
  7. customrecrystallised from ethylacetate/heptane

Sources & evidence

ORD record
ord-c78c197e9a27407281495cf1efaebdd0
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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