Hydrochloric Acid → HCID 22419955, compound

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.

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%

ORD record

ord-c17aa2d6fc814f1f929304cb1ce040e6

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05504101