Dabco → HCID 69518032, compound

HRID 1179945Notes

Reaction equation

HRID 1179945 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 recrystalllised 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

Sources & evidence

ORD record
ord-2b120c51c31b4f24b90f45764ac38316
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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