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

HRID 39755

反応式

HRID 39755 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-959d4246b23d4fff8931afb03244c7ba
出典データセット
uspto-grants-2013_09
特許番号
US08524738B2

関連ノート

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