78283-29-1

Upstream product

• 123-75-1 pyrrolidine 
• 20876-37-3 2-benzyloxy-6-nitrotoluene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 100-39-0 benzyl bromide 
• 5460-31-1 3-nitro-o-cresol 

Downstream Products

• 78283-32-6 2-benzyloxy-6-nitrophenyl acetaldehyde dimethyl acetal 
• 78283-31-5 1-acetoxy-4-benzyloxyindole 
• 2380-94-1 1H-indol-4-ol 
• 78283-30-4 2-benzyloxy-6-nitrophenyl acetaldehyde 
• 20289-26-3 4-benzyloxy-1H-indole 
• 78283-33-7 4-benzyloxy-2-(4-benzyloxyindol-3-yl)-2,3-dihydroindole 

Relevant academic research and scientific papers

SYNTHESIS OF 4-SUBSTITUTED INDOLES FROM o-NITROTOLUENES

A facile two- or three-step transformation of o-nitrotoluenes into 4-substituted indoles is described.Treatment of o-nitrotoluenes 1 with DMF acetal, or sometimes more advantageously with tris(N,N-dimethylamino)methane, affords β-(N,N-dimethylamino)styrenes 2 which are readily converted too-nitrophenylacetaldehyde semicarbazones 3 without isolation.Reduction of either 2 or 3 affords 4-substituted indoles 4.Use of the very insoluble semicarbazones results in vastly superior yields of 4 by minimizing completing bimolecular condensation reactions during reduction.This new procedure has been applied to efficiently and conveniently prepare a series of 4-substituted indoles 4.