Reaktion #54673

Reaktionsgleichung

ethyl-7-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate

methylamine

→

3,9b-Dimethyl-3a-hydroxy-8-methoxy-2-oxo-2,3,3a,4,5,9b-hexahydro-1H-benz[e]indole

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crystalline precipitate formed
2. 2
   Sonstigewas separated
3. 3
   Sonstigeto give 15.5 g (74.5%) Xb, m.p. 182°-186°
4. 4
   SonstigeFrom the mother liquor, after evaporation (35°) and treatment with ether, 1.0 g, additional Xb
5. 5
   Sonstigewas collected
6. 6
   Temperaturincreasing the
7. 7
   Sonstigeyield to 79.5%

Vorschrift

The solution of 22.0 g (79.7 mmol) ethyl-7-methoxy-1-methyl-2-oxo-1,2,3,4-tetrahydro-1-naphthaleneacetate (IXb) and 7.5 g (240 mmol) methylamine in 25 ml ethanol was left at room temperature for 24 hr. The crystalline precipitate formed was separated to give 15.5 g (74.5%) Xb, m.p. 182°-186°. From the mother liquor, after evaporation (35°) and treatment with ether, 1.0 g, additional Xb was collected increasing the yield to 79.5%; IR (Nujol), 3300 (OH), 1670 cm-1 (lactam); NMR (CDCl3 -DMSO) δ, 1.48 (s, 3, CH3), 2.82 (s, 3, N--CH3), 3.78 (s, 3, OCH3), 6.6-7.1 (m, 3, ArH).

Quelle