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- W2012359178 abstract "In second-order Beckmann reactions oximes of the title compound (1) and 1-[2-(N,N-dimethylamino)ethyl]-3,4-dihydro-1-methylnaphthalen-2(1H)-one (14) gave 1,2,3,4-tetrahydro-3,6-dimethyl-3-benzazocine-2-carbonitrile (8) and (E)-2-[o-(2-cyanoethyl)phenyl]-4-dimethylaminobut-2-ene (15), respectively. The benzazocine-2-carbonitrile (8) was hydrolysed to the corresponding carboxylic acid (10), which was converted into its ethyl (11) and methyl esters (12) and reduced to the 2-aminomethyl-3-benzazocine (13). An attempt to prepare the ethyl ester (11) in hot 10% aqueous ethanol saturated with hydrogen chloride resulted in ring contraction, to give 1-methyl-2-(N-methylaminomethyl)naphthalene (17). In a Pinner reaction in ethanol the benzazocine-2-carbonitrile (8) gave the corresponding amide (9) instead of the ethyl imidate." @default.
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- W2012359178 date "1983-01-01" @default.
- W2012359178 modified "2023-10-16" @default.
- W2012359178 title "Synthesis and reactions of 1,2,3,4,5,6-hexahydro-3,6-dimethyl-2,6-methano-3-benzazocin-11-one (2,5-dimethyl-9-oxo-6,7-benzomorphan); a new route to 3-benzazocines" @default.
- W2012359178 doi "https://doi.org/10.1039/p19830002583" @default.
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