32989-62-1

Basic information

• Product Name: Ethenamine, 2-(5-methoxy-2-nitrophenyl)-N,N-dimethyl-, (E)-
• Synonyms: trans-β-(dimethylamino)-5-methoxy-2-nitrostyrene;trans-β-dimethylamino-5 -methoxy-2-nitrostyrene;trans-β-dimethylamino-5-methoxy-2-nitrostyrene
• CAS NO: 32989-62-1
• Molecular Formula: C11H14N2O3
• Molecular Weight: 222.244
• Mol File: 32989-62-1.mol

Chemical Properties

• CAS DataBase Reference: Ethenamine, 2-(5-methoxy-2-nitrophenyl)-N,N-dimethyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethenamine, 2-(5-methoxy-2-nitrophenyl)-N,N-dimethyl-, (E)-(32989-62-1)
• EPA Substance Registry System: Ethenamine, 2-(5-methoxy-2-nitrophenyl)-N,N-dimethyl-, (E)-(32989-62-1)

Safety Data

• Hazardous Substances Data: 32989-62-1(Hazardous Substances Data)

Upstream product

• 5367-32-8 5-methoxy-2-nitrotoluene 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 2581-34-2 3-methyl-4-nitrophenol 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 56995-12-1 1-benzenesulfonyl-5-methoxy-1H-indole 
• 143706-87-0 3-carboxy-4-pyridyl 1'-(phenylsulfonyl)-5'-methoxy-2'-indolyl ketone 
• 1006-94-6 5-methoxylindole 

Relevant articles and documents

Microwave assisted Leimgruber-Batcho reaction for the preparation of indoles, azaindoles and pyrroylquinolines

The development of enhanced conditions for Lewis acid catalysed Leimgruber-Batcho indole synthesis using microwave acceleration is described. This approach has permitted the preparation of a variety of heteroaromatic enamine intermediates in good yield and high purities. Subsequent catalytic hydrogenation reactions, under various conditions including the use of a solid-phase encapsulated catalyst, furnish the corresponding indole derivatives in good yields.

A Versatile and Efficient Construction of the 6H-Pyridocarbazole Ring System. Syntheses of the Antitumor Alkaloids Ellipticine, 9-Methoxyellipticine, and Olivacine and Their Analogues

A general and efficient synthesis of the 6H-pyridocarbazole ring system is described, in which the key steps are (1) regioselective acylation of a 2-lithio-1-(phenylsulfonyl)indole (14) with 3,4-pyridinedicarboxylic acid anhydride (10), (2) cyclization of the deprotected keto acid 17 to keto lactam 19 with acetic anhydride, and (3) the addition of methyllithium to give, after reduction of the intermediate diol 23 with sodium borohydride, the target ring system.In this fashion, ellipticine (1a), 9-methoxyellipticine (1b), and 9-hydroxyellipticine (1c) were synthesized in excellent overall yields from indole.The use of Superhydride, in place of 1 equiv of methyllithium, provided a synthesis of olivacine (2), and the use of phthalic anhydride in the sequence allowed for the preparation of 6,11-dimethylbenzocarbazole (48).The overall yields of ellipticine (1a) (54percent) and 9-methoxyellipticine (1b) (47percent) in six steps from their respective indoles represent one of the most efficient syntheses of these antitumor alkaloids.

Intermediates for indoles

Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.