Réaction #53619

Équation de réaction

sodium hydrogencarbonate

Triethylamine

trichloroacetyl chloride

compound ( 47 )

8-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulene-5-carbaldehyde Oxime

→

titled compound

Rendement 98.0%

8-Dimethylamino-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]-azulene-5-carbonitrile

Rendement 98.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   ExtractionThe mixture was extracted with chloroform
2. 2
   LavageThe extracts were washed with brine
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutreThe residue obtained
6. 6
   Autrewas chromatographed on aluminum oxide in chloroform:methanol (97:3)

Mode opératoire

Triethylamine 33 μl and trichloroacetyl chloride 13 μl were added to a solution of compound (47) 28.9 mg in dichloromethane 2 ml with cooling ice and the mixture was stirred with cooling in ice and at room temperature for 18 h. A saturated sodium hydrogencarbonate solution was added thereto for alkalinization. The mixture was extracted with chloroform. The extracts were washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform:methanol (97:3) to give the titled compound 26.3 mg as colorless crystals. Yield 98%. Furthermore, the titled compound was recrystallized from methanol-isopropyl ether to give colorless crystals, m.p. 205-207° C.

Source