Imidazole → 1-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one

HRID 39697

Reaction equation

HRID 39697 reaction equation
CN(C)C=O.[H-].[Na+].[NH:8]1[CH:12]=[CH:11][N:10]=[CH:9]1.Br[C:14]1[CH:23]=[C:22]2[C:17]([C:18]([CH3:31])=[CH:19][C:20](=[O:30])[N:21]2[CH2:24][CH:25]2[O:29][CH2:28][CH2:27][O:26]2)=[CH:16][CH:15]=1>[Cu]=O.O.C(Cl)(Cl)Cl>[O:26]1[CH2:27][CH2:28][O:29][CH:25]1[CH2:24][N:21]1[C:22]2[C:17](=[CH:16][CH:15]=[C:14]([N:8]3[CH:12]=[CH:11][N:10]=[CH:9]3)[CH:23]=2)[C:18]([CH3:31])=[CH:19][C:20]1=[O:30]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 593980747-Bromo-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1h)-one

Product 1

HCID 593979121-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
142.5 °C

Procedure

To 0.7 mL of an N,N-dimethylformamide solution containing 74 mg of 60% sodium hydride, 0.14 g of imidazole was added at room temperature, and the mixture was stirred for 10 minutes. Thereto were added 0.20 g of 7-bromo-1-(1,3-dioxolan-2-ylmethyl)-4-methylquinolin-2(1H)-one and 17 mg of copper(II) oxide, and the mixture was heated to 140 to 145° C. and stirred for 40 minutes. Thereto was further added 2 mL of N,N-dimethylformamide, and the mixture was further stirred for 1 hour. The reaction mixture was cooled to room temperature, then chloroform and water were added thereto, and the insoluble material filtered off. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to obtain 77 mg of a brown oily substance, 1-(1,3-dioxolan-2-ylmethyl)-7-(1H-imidazol-1-yl)-4-methylquinolin-2(1H)-one.

Workup

  1. additionwas added at room temperature
  2. stirringstirred for 40 minutes
  3. stirringthe mixture was further stirred for 1 hour
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationthe insoluble material filtered off
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with chloroform
  8. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

Sources & evidence

ORD record
ord-440530fd2e514d4ca5b600297af91348
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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