Anilides, Aminoethyl Ethers and Acetylation Products of 6-Amino-4-methylsalicylates

Article abstract of DOI:10.1002/ardp.19803130803

6-Dialkylamino-4-methylsalicylates 1 yield the anilides 2 on heating with substituted anilines.Methyl 4-methyl-6-morpholinosalicylate (4), after conversion into the phenolate, undergoes condensation with (β-chloroethyl)dialkylamines to give dialkylaminoethylphenylethers of type 3.The 6-monoalkylamino-4-methylsalicylate 8c is acylated with an equimolar amount of acetic anhydride to give the N-acyl derivative 8d, whereas two equivalents afford the N,O-diacyl derivative 8e.Analogous results have been obtained for the 3-amino-4-methyl-6-morpholinosalicylates 6c and 7c.