Hydrochloric Acid → 3-Benzyl-5,6,7,8-tetrahydroquinoxalin-2(1H)-one

HRID 330071ノート

反応式

HRID 330071 の反応式
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=O.Cl.[NH2:10][C@H:11]([C:19]([NH2:21])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[OH:20][C:19]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=2[N:21]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 130061,2-CyclohexanedioneHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 11953719Phenylalanine amide hydrochloride

生成物 1

HCID 1785173403-Benzyl-5,6,7,8-tetrahydroquinoxalin-2(1H)-one収率 82.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A methanol (30 ml) solution of cyclohexane-1,2-dione (13.44 g, 0.12M) was added to phenylalanineamide hydrochloride (20.05 g, 0.1M) dissolved in methanol (200 ml) with cooling below -30° C., and aqueous 12.5N-NaOH (20 ml) was added dropwise thereto. The reaction mixture was stirred at below -30° C. for 30 minutes and was further stirred at room temperature for 3 hours. Conc. hydrochloric acid (25 ml) was added to the reaction mixture, and sodium bicarbonate (15 g) was added after 10 minutes stirring, the solvent then being distilled off in vacuo. The residue, to which was added water, was extracted three times with chloroform, and the extract was dried with anhydrous magnesium sulfate and concentrated in vacuo. The residue was recrystallized from acetone to obtain the product. (19.7 g, yield: 82.1%).

後処理

  1. temperaturewith cooling below -30° C.
  2. stirringwas further stirred at room temperature for 3 hours
  3. additionwas added after 10 minutes
  4. stirringstirring
  5. distillationthe solvent then being distilled off in vacuo
  6. additionThe residue, to which was added water
  7. extractionwas extracted three times with chloroform
  8. dry with materialthe extract was dried with anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from acetone
  11. customto obtain the product

出典と根拠

ORDレコード
ord-72db7c37bcbc4fa48068c74312bc73c5
出典データセット
uspto-grants-1990_01
特許番号
US04894453

反応ノート

読み込み中…