Hydrochloric Acid → HCID 22419955、化合物

HRID 1720068ノート

反応式

HRID 1720068 の反応式
N([O-])=O.[Na+].Cl.[CH2:6]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH3:22][CH:23](C(C)=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25].[OH-].[K+].[Cl-].[NH4+]>O.CCO>[CH2:27]([O:26][C:24]([C:23]1[C:16]2[C:17](=[CH:19][CH:20]=[C:14]([CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:15]=2)[NH:18][CH:22]=1)=[O:25])[CH3:28]

参加物

9

反応物 6

HCID 313Hydrochloric Acid2 回HCID 701Ethyl 2-methylacetoacetateHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 224199564-Phenethylaniline HydrochlorideHCID 23668193Sodium Nitrite

生成物 1

HCID 22419955HCID 22419955、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

Solid NaNO2 (0.35 g, 5 mmol) was added to a suspension of the p-phenethylaniline hydrochloride (1.1 g, 5 mmol) and concentrated HCl (2 ml) in H2O (3 ml) under an icewater bath. The solution was kept at -5° C. with stirring while ethyl 2-methylacetoacetate (0.72 g, 5 mmol)in EtOH 95% (5 ml) was treated at -10° C. with a solution of 50% KOH (1.7 ml) followed at once by ice (10 g). The diazo-solution was then added immediately, stirred at room temperature for 20 min, and extracted with Et2O (2×20 ml). The combined Et2O portions were dried (MgSO4) and the solvent was removed under reduced pressure to give a red oil which was taken up in anhydrous EtOH (10 ml), and dry hydrogen chloride gas was passed through the solution until ammonium chloride was precipitated. The mixture was heated at reflux for 20 min, and then stirred at room temperature for 2 h. The suspension was poured into ice water (100 ml) and extracted with Et2O (2×30 ml). The combined Et2O portions were dried (MgSO4) and the solvent was removed under reduced pressure to give a solid which was recrystallized from EtOH 95% to provide 3-ethyloxycarbonyl-5-(2-phenylethyl)indole.

後処理

  1. customwas kept at -5° C.
  2. extractionextracted with Et2O (2×20 ml)
  3. dry with materialThe combined Et2O portions were dried (MgSO4)
  4. customthe solvent was removed under reduced pressure
  5. customto give a red oil which
  6. customwas precipitated
  7. temperatureThe mixture was heated
  8. temperatureat reflux for 20 min
  9. stirringstirred at room temperature for 2 h
  10. additionThe suspension was poured into ice water (100 ml)
  11. extractionextracted with Et2O (2×30 ml)
  12. dry with materialThe combined Et2O portions were dried (MgSO4)
  13. customthe solvent was removed under reduced pressure
  14. customto give a solid which
  15. customwas recrystallized from EtOH 95%

出典と根拠

ORDレコード
ord-c17aa2d6fc814f1f929304cb1ce040e6
出典データセット
uspto-grants-1996_04
特許番号
US05504101

反応ノート

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