55786-24-8

Basic information

• Product Name: 7,8-DEHYDRORUTAECARPINE
• Synonyms: 7,8-DEHYDRORUTAECARPINE
• CAS NO: 55786-24-8
• Molecular Formula: C₁₈H₁₁N₃O
• Molecular Weight: 285.29944
• Mol File: 55786-24-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 279.5-280.5 °C(Solv: 1,2-dichloroethane (107-06-2))
• Boiling Point: 560.7°Cat760mmHg
• Flash Point: 292.9°C
• Appearance: /
• Density: 1.44g/cm³
• PKA: 15.76±0.20(Predicted)
• CAS DataBase Reference: 7,8-DEHYDRORUTAECARPINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7,8-DEHYDRORUTAECARPINE(55786-24-8)
• EPA Substance Registry System: 7,8-DEHYDRORUTAECARPINE(55786-24-8)

Safety Data

• Hazardous Substances Data: 55786-24-8(Hazardous Substances Data)

Upstream product

• 33284-02-5 2-amino-N-[2-(1H-indol-3-yl)ethyl]benzamide 
• 68-12-2 N,N-dimethyl-formamide 
• 3724-43-4 Vilsmeier reagent 
• 118-48-9 isatoic anhydride 
• 61-54-1 tryptamine 
• 38750-16-2 Rutaecarpene 
• 98260-32-3 2-chloro-3-<2-(indol-3-yl)ethyl>-4(3H)-quinazolinone 

Relevant articles and documents

Bicyclic 1,2,3-triazolium ionic liquids: Synthesis, characterization, and application to rutaecarpine synthesis

Starting with commercial reagents, bicyclic 1,2,3-triazolium ionic liquids [b-3C-tr][NTf2] (1) and [b-4C-tr][NTf2] (2) were synthesized in four steps with high overall isolated yields of 68% and 76%, respectively. Since the C-5 hydrogen is acidic, under basic condition ionic liquids 1 and 2 were readily methylated with methyl iodide to afford chemically stable ionic liquids 7 and 8 at room temperature (88% and 82%, respectively). Ionic liquid 1 was used as the ionic solvent to demonstrate its usefulness for the synthesis of rutaecarpine, a natural product.

A New Synthesis of Rutecarpine

1,2,3,4-Tetrahydro-β-carboline (1) reacts with 2-nitrobenzyl chloride to yield the tertiary amine 2, which on reduction of the nitro group and dehydrogenating cyclization yields the pentacyclic amidine 4.Oxidation of 4 produces a mixture of rutecarpine (5) and the dehydrogenation compound 6, which are separated by chromatography.