合成路线:The Sandmeyer reaction of 4-aminophenyl-alpha-methylacetonitrile (I) with NaNO2,HCl and H2SO4 gives 4-hydroxyphenyl-alpha-methylacetonitrile (II),which is nitrated with nitric acid in acetic acid yielding 4-hydroxy-3-nitrophenyl-alpha-methylacetonitrile (III).The reduction of (III) with SnCl2.2H2O and HCl in ethanol,or with H2 over Pd/C in the same solvent affords 4-hydroxy-3-aminophenyl-alpha-methylacetonitrile (IV),which is hydrolyzed with refluxing concentrated HCl to 4-hydroxy-3-aminophenyl-alpha-methylacetic acid (V).The esterification of (V) with ethanol and HCl affords the corresponding ethyl ester (VI),which is cyclized with p-chlorobenzoyl chloride (VII) in pyridine at 100 C yielding ethyl 2-(4-chlorophenyl)-alpha-methyl-5-benzoxazoleacetate (VIII).Finally,this compound is hydrolyzed with NaOH in ethanol.
参考文献标题:2-Aryl-5-benzoxazolealkanoic acid derivatives with notable antiinflammatory activity
文献作者:Dunwell,D.W.; Evans,D.; Hicks,T.A.
参考来源:J Med Chem 1975,18(1),53
合成路线:The Sandmeyer reaction of 4-aminophenyl-alpha-methylacetonitrile (I) with NaNO2,HCl and H2SO4 gives 4-hydroxyphenyl-alpha-methylacetonitrile (II),which is nitrated with nitric acid in acetic acid yielding 4-hydroxy-3-nitrophenyl-alpha-methylacetonitrile (III).The reduction of (III) with SnCl2.2H2O and HCl in ethanol,or with H2 over Pd/C in the same solvent affords 4-hydroxy-3-aminophenyl-alpha-methylacetonitrile (IV),which is hydrolyzed with refluxing concentrated HCl to 4-hydroxy-3-aminophenyl-alpha-methylacetic acid (V).The esterification of (V) with ethanol and HCl affords the corresponding ethyl ester (VI),which is cyclized with p-chlorobenzoyl chloride (VII) in pyridine at 100 C yielding ethyl 2-(4-chlorophenyl)-alpha-methyl-5-benzoxazoleacetate (VIII).Finally,this compound is hydrolyzed with NaOH in ethanol.
参考文献标题:Benoxaprofen
文献作者:Castar,J.; Blancafort,P.
参考来源:Drugs Fut 1977,2(9),565
产品链接: CAS No. 51234-28-7››