108439-54-9

Basic information

• Product Name: 1-(3-ethoxy-4-methoxybenzylamino)cyclohexanecarbonitrile
• CAS NO: 108439-54-9
• Molecular Weight: 288.39
• Mol File: 108439-54-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(3-ethoxy-4-methoxybenzylamino)cyclohexanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-ethoxy-4-methoxybenzylamino)cyclohexanecarbonitrile(108439-54-9)
• EPA Substance Registry System: 1-(3-ethoxy-4-methoxybenzylamino)cyclohexanecarbonitrile(108439-54-9)

Safety Data

• Hazardous Substances Data: 108439-54-9(Hazardous Substances Data)

Upstream product

• 151-50-8 potassium cyanide 
• 108-94-1 cyclohexanone 
• 108439-67-4 3-ethoxy-4-methoxybenzylamine 

Relevant articles and documents

The Cyclisation of Benzylaminonitriles. Part 6. Evidence for Exclusive Participation of a Spirocyclic Intermediate

Cyclisation of 3,4-dialkoxybenzylaminoacetonitriles to 6,7-dialkoxy-1,2-dihydroisoquinolin-4(3H)-ones can occur by two mechanisms.The first involves electrophilic attack para to the 3-alkoxy substituent, and the second proceeds via formation of a spirocyclic intermediate with the participation of the 4-alkoxy group.In order to assess the relative contribution of these two mechanisms the cyclisation of 1-(4-ethoxy-3-methoxybenzylamino)cyclohexanecarbonitrile (12) and the isomer with the reverse orientation of alkoxy substituents (13) was studied.The benzylamino nitrile (12) on treatment with concentrated sulphuric acid at -10 deg C, room temperature, and 50 deg C gave a mixture of the 7-ethoxy-6-methoxyisoquinolinone (27) and the 7-hydroxy-6-metoxyisoquinolinone (26).Identical treatment of the isomeric 3-ethoxy-4-methoxybenzylamino nitrile (13) produced the 6-ethoxy-7-methoxyisoquinolinone (28), the 6-hydroxy-7-methoxyisoquinolinone (29), and the 6-ethoxy-7-hydroxyisoquinolinone (30).The relative proportion of phenolic products increased with rise in temperature of cyclisation.The profile of O-dealkylation that occured during cyclisation differed from that of the 6,7-dialkoxyisoquinolinones under identical conditions, and a case is argued that cyclisation proceeds no further than the spirocyclic intermediate in concentrated acid.Rearrangement to the iminium ion and conversion of the latter into the isoquinolinone via a Pictet-Spengler reaction therefore occur during subsequent stages in dilute aqueous conditions.