91523-31-8

Basic information

• Product Name: Benzenepropanamide, N-chloro-N-methoxy-
• CAS NO: 91523-31-8
• Molecular Formula: C10H12ClNO2
• Molecular Weight: 213.664
• Mol File: 91523-31-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzenepropanamide, N-chloro-N-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanamide, N-chloro-N-methoxy-(91523-31-8)
• EPA Substance Registry System: Benzenepropanamide, N-chloro-N-methoxy-(91523-31-8)

Safety Data

• Hazardous Substances Data: 91523-31-8(Hazardous Substances Data)

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 112403-99-3 potassium cinnamohydroxamate 
• 112404-04-3 O-methyl cinnamohydroxamate 
• 23601-49-2 O-methyl 3-phenylpropanohydroxamate 

Downstream Products

• 91523-37-4 N-methoxy-3,4-dihydro-1H-quinolin-2-one 
• 112403-88-0 O-methyl N-phenyl-3-phenylpropanohydroxamate 
• 23601-49-2 O-methyl 3-phenylpropanohydroxamate 

Relevant articles and documents

Intramolecular Cyclization with Nitrenium Ions Generated from N-Chloro-N-methoxyamides in Neutral Conditions

Intramolecular aromatic substitution by a N-chloro-N-methoxyamide group to a suitably situated aromatic ring in the molecule is performed by using anhydrous zinc acetate and nitromethane as solvent to give nitrogen heterocycles in good yield.

A new synthesis of N-alkoxy-2-ethoxyarylacetamides from N-alkoxy-N-chloroarylacetamides with triethylamine in ethanol

Treatment of N-alkoxy-N-chloroarylacetamides with triethylamine in ethanol results in removal of a chlorine atom and introduction of an ethoxy group at the C-2 position of arylacetamides in moderate yields.

N-ALKOXY-N-ACYLNITRENIUM IONS IN INTRAMOLECULAR AROMATIC ADDITION REACTIONS

N-alkoxy-N-acylnitrenium ions are generated by treatment of N-alkoxy-N-chloroamides with silver ions in ethereal solvents.These intermediates readily cyclise onto aromatic nuclei on alkoxy side-chains to give benzoxazines and benzoxazepines and on the acyl side-chains to give γ, δ and ε benzolactams.Spirane products are formed by ipso addition when a 4-methoxy substituent is present on the side-chain aromatic rings.The yields and regioselectivities of these reactions have been ascribed to different transition structures for cyclisation onto the acyl and alkoxy side-chains which involve respectively an exocyclic and endocyclic N-O ?-bond.Evidence for this exeptionally high ?-bond character has been obtained from MNDO calculations which predict a ?-bond order of 0.9 and a rotational barrier of 29.7 kcalmol-1