Intermediates in nucleophilic aromatic substitution. X. Synthesis of N-methyl-. beta.-aminoethyl nitroaryl ethers via an unusual Smiles rearrangement

CF Bernasconi, RH De Rossi…

Index: Bernasconi,C.F. et al. Journal of Organic Chemistry, 1973 , vol. 38, p. 2838 - 2842

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Citation Number: 28

Abstract

Method A.-A solution of 0.5 g of 2c in 50 ml of hot alcohol was treated with 2 g of sodium sulfide, refluxed overnight, and filtered; the hot filtrate was diluted with water and chilled. The solid was collected and crystallized from aqueous alcohol giving 0.3 g of 15: mp 107-108'; mass spectrum m/e 337 (loo), 336 (52), 232 (19), 230 (14), 168.5, 115 (7), 105 (26), and 77 (24).