95274-55-8

Basic information

• Product Name: 4(3H)-Quinazolinone, 3-[2-(1H-indol-3-yl)ethyl]-2-(trichloromethyl)-
• CAS NO: 95274-55-8
• Molecular Formula: C19H14Cl3N3O
• Molecular Weight: 406.699
• Mol File: 95274-55-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4(3H)-Quinazolinone, 3-[2-(1H-indol-3-yl)ethyl]-2-(trichloromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(3H)-Quinazolinone, 3-[2-(1H-indol-3-yl)ethyl]-2-(trichloromethyl)-(95274-55-8)
• EPA Substance Registry System: 4(3H)-Quinazolinone, 3-[2-(1H-indol-3-yl)ethyl]-2-(trichloromethyl)-(95274-55-8)

Safety Data

• Hazardous Substances Data: 95274-55-8(Hazardous Substances Data)

Upstream product

• 33284-02-5 2-amino-N-[2-(1H-indol-3-yl)ethyl]benzamide 
• 79-22-1 methyl chloroformate 
• 41470-85-3 2-trichloromethyl-benzo[d][1,3]oxazin-4-one 
• 61-54-1 tryptamine 

Relevant articles and documents

Studies of Rutaecarpine and Related Quinazolinocarboline Alkaloids

Quinazolinocarboline alkaloids, e.g., rutaecarpine (1), can readily be synthesized by treating tryptamine with 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (quickly generated in situ from trifluoroacetic anhydride (TFAA) and 2H-3,1-benzoxazine-2,4(1H)-dione.The product formed, 3--2-(trifluoromethyl)-4-(3H)-quinazolinone (5), is then cyclized (HCl/HOAc) to 13b-(trifluoromethyl)-13b,14-dihydrorutaecarpine (6), whereupon CF3H is eliminated by treatment with base.The sequence can conveniently be performed as a three-reaction one-pot procedure giving rutaecarpine (1) in 99percent yield within 3h.The approach can readily be extended to the synthesis of evodiamine (2), 13,13b-dehydroevodiamine (38a), and 13b,14-dihydrorutaecarpine (21).Thus treatment of 3--4(3H)-quinazolinone (19) with TFAA affected cyclization to 13b-(trifluoroacetyl)-13b,14-dihydrorutaecarpine (20), which can be readily hydrolyzed to 13b,14-dihydrorutaecarpine (21).