Reaktion #2484254

Reaktionsgleichung

diethyl 2-(5H-dibenzo[a,d]cyclohepten-5-yl)-2-acetamidomalonate

sodium hydroxide

methanol

HCl

→

5H-dibenzo[a,d]cyclohepten-5-ylglycine

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 8h
3. 3
   EinengenThe solution was concentrated in vacuo
4. 4
   workup.ADDITIONacidified to pH=2 by addition of 1M-HCl
5. 5
   SonstigeThe solid which formed
6. 6
   Filtrationwas collected by filtration
7. 7
   FiltrationThe cooled solution was filtered
8. 8
   workup.DISSOLUTIONthe residue dissolved in hot water
9. 9
   workup.ADDITIONwas added aqueous ammonia until pH 7-8
10. 10
    SonstigeThe solid which formed
11. 11
    Temperaturon cooling to room temperature
12. 12
    Filtrationwas collected by filtration
13. 13
    Sonstigedried in vacuo

Vorschrift

A mixture of diethyl 2-(5H-dibenzo[a,d]cyclohepten-5-yl)-2-acetamidomalonate (20.2g, Example 1b) and sodium hydroxide (4g) in methanol (75ml) and water (75ml) was heated to reflux for 8h. To the cooled solution was added 1M-HCl until pH=6. The solution was concentrated in vacuo and acidified to pH=2 by addition of 1M-HCl. The solid which formed was collected by filtration and heated together with 6M-HCl for 3h at 100° C. The cooled solution was filtered and the residue dissolved in hot water, refiltered and to the filtrate was added aqueous ammonia until pH 7-8. The solid which formed on cooling to room temperature was collected by filtration and dried in vacuo to give 5H-dibenzo[a,d]cyclohepten-5-ylglycine. 1H NMR (360MHz, d4MeOH), δ 4.08-4.12 (1H, m), 4.35-4.39 (1H, m), 7.0-7.11 (2H, m), 7.24-7.30 (3H, m), 7.34-7.45 (5H, m).

Quelle