Hydrochloric Acid → 4-Acetyl-1-(1,3-dioxolan-2-ylmethyl)-2-oxo-3,4-dihydro-1h-quinoxaline

HRID 2193126

Reaction equation

HRID 2193126 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:18][CH:19]1[O:23][CH2:22][CH2:21][O:20]1.Cl>C(OCC)(=O)C.CN(C)C=O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:18][CH:19]2[O:23][CH2:22][CH2:21][O:20]2)[C:6](=[O:14])[CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 27708254-Acetyl-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 593981594-Acetyl-1-(1,3-dioxolan-2-ylmethyl)-2-oxo-3,4-dihydro-1h-quinoxaline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 15 mL of an N,N-dimethylformamide solution containing 957 mg of 4-acetyl-3,4-dihydro-2-oxo-1H-quinoxaline, 668 mg of sodium hydride was added, and the mixture was stirred at room temperature for 1 hour. Thereto was added 2.6 mL of 2-bromomethyl-1,3-dioxolane, and the mixture was stirred at 90° C. for 6 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and 1 mol/L hydrochloric acid were added thereto. The organic layer was separated, washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; chloroform] to obtain 1.30 g of a brown oily substance, 4-acetyl-1-(1,3-dioxolan-2-ylmethyl)-2-oxo-3,4-dihydro-1H-quinoxaline.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 90° C. for 6 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. washwashed sequentially with water
  6. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [silica gel; Silica gel 60 manufactured by Kanto Chemical Co., Inc., eluent; chloroform]

Sources & evidence

ORD record
ord-b9aeda3f88744744bf8f74b7be62b48f
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Linked notes

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