2-(n,n-dialkyl-and n-alkoxy-n-alkyl-carbamoyl-methoxy)-benzoic acid esters substituted in the 5-position

摘要

Novel compounds of Formula I FORM:1081245/C2/1 wherein R is an alkyl radical having up to 6 carbon atoms, and R1 is an alkyl or alkoxy radical having up to 6 carbon atoms, or R and R1 together with the nitrogen atom and possibly also an oxygen atom form a saturated heterocyclic ring, R11 is an alkyl or alkenyl radical having up to 6 carbon atoms, and R111 is a saturated or unsaturated aliphatic, aliphatic-oxy, aliphatic-oxy-aliphatic, hydroxy-aliphatic or oxo-aliphatic radical having up to 6 carbon atoms, may be prepared (1) by reacting a 5-substituted salicylic acid ester in the presence of condensation agents with a glycollic acid amide of formula HO-CH2-CONRR1 or a reactive ester thereof, (2) by reacting a 5-substituted 2 - carboxymethoxybenzoic acid ester or a reactive functional derivative thereof with an amine of formula R-NH-R1 or a reactive derivative thereof, (3) when R111 represents an alkyl group, by alkylation of the corresponding hydroxy compound, or (4) by reducing the corresponding carboxyaldehyde to give compounds in which R111 represents a hydroxymethyl or methyl radical, or by reacting the aldehyde with a lower aliphatic ketone to give compounds in which R111 represents an oxoalkenyl radical, which may be converted into an oxoalkyl, hydroxyalkenyl, hydroxyalkyl or alkyl radical. The esters of the invention may also be obtained by esterification of the corresponding acid, acid chloride, mixed anhydride or salt, or by transesterification of other esters. Methyl 5-n-propyloxysalicylate may be obtained by treating hydroquinone mono-n-propyl ether with carbon dioxide under pressure and esterifying the 5-n-propylsalicylic acid obtained. Methyl 5-acetylsalicylate is obtained by esterification of the free acid. Other alkyl 5-propionylsalicylates may be obtained by Frie's rearrangement of the alkyl O-propionylsalicylate. n-Propyl 2-carboxymethoxy-5-ethoxy-benzoate is made by reacting n-propyl 5-ethoxysalicylate with sodium chloroacetate and releasing the free acid from the sodium salt obtained.