80573-82-6

Upstream product

• 700-75-4 2-methoxy-N,N-dimethyl-benzenamine 
• 106-95-6 allyl bromide 
• 91-16-7 1,2-dimethoxybenzene 

Downstream Products

• 700-75-4 2-methoxy-N,N-dimethyl-benzenamine 
• 15258-52-3 N-allyl-N-methyl-o-anisidine 
• 80573-86-0 3-allyl-2-dimethylaminoanisole 

Relevant academic research and scientific papers

Oxyaniliniums as acetylcholinesterase inhibitors for the reversal of neuromuscular block

A series of oxyanilinium-based AChE inhibitors have been synthesised and tested for the reversal of vecuronium-induced neuromuscular block. Several compounds, for example 2-hydroxy- and 2-methoxy-N,N-dimethyl-N-allylanilinium bromide (3 and 6) showed comparable reversal potencies to edrophonium and clean in vivo cardiovascular profiles.

AMINO-CLAISEN REARRANGEMENT. II. QUATERNARY AMINO-CLAISEN REARRANGEMENT OF ANILINIUM COMPOUNDS WITH ORTHO SUBSTITUENTS

Amino(N)-Claisen rearrangement of quaternary aniline derivatives with ortho substituents was investigated in relation to that of corresponding tertiary anilines.N-allylated anilinium compounds 1 with a freely rotating ortho substituent such as a methyl or methoxy group yielded mostly the deallylated products 4 along with minor amounts of rearrangement products 2 and 3.The corresponding tertiary anilines yielded ortho rearrangement products 6 together with para ones 7.The quaternary N-Claisen rearrangement of N-allylated 1,2,3,4-tetrahydroquinolinium salts 14 and indolinium salts 22 in which the ortho substituents are locked in rings afforded the ortho rearrangement products 15 and 23, respectively in good yields.N-Claisen rearrangement of the corresponding aromatic tertiary amines 18 also took place in good yield.The above rearrangements could be rationalized on the basis of mechanistic considerations.Keywords: - quaternary amino-Claisen rearrangement; mechanism; sigmatropic rearrangement; N-allyl-N,N-dimethyl-o-toluidinium bromide; N-allyl-N,N-dimethyl-o-anisidinium bromide; 1-allyl-1-methyl-1,2,3,4-tetrahydroquinolinium halides; 1-allyl-1,2-dimethylindolinium bromide; 8-allyl-1-methyl-1,2,3,4-tetrahydroquinoline; 6-allyl-1-methyl-1,2,3,4-tetrahydroquinoline; 7-allyl-1,2-dimethylindoline