合成路线:4-Benzyloxy-indole-2-carboxylic acid (I) is converted into the corresponding dimethylamide (III),via the corresponding acid chloride (II); the dimethylamide (III) is reduced with LiAlH4 to give 4-benzyloxy-2-dimethylaminomethyl-indole (IV),which is hydrogenated to 4-hydroxy-2-methyl-indole (V).The reaction of (V) with epichlorohydrin (A) in aqueous NaOH gives the crude epoxide which without isolation is treated with isopropylamine (B) in refluxing dioxane.
合成路线:4-Hydroxy-2-methyl-indole (IV) can be quaternized with MeI yielding the ammonium salt (VI),which by heating with aqueous NaCN in converted into 2-cyanomethyl-4-benzyloxyindole (VII).The hydrolysis of (VII) affords the corresponding acid (VIII),which is decarboxylated to 4-benzyloxy-2-methyl-indole (IX).Finally,this compound is hydrogenated to the previously obtained 4-hydroxy-2-methyl-indole (V).
参考文献标题:Verfahren zur Herstellung neuer Indolderivate
文献作者:Troxler,F.; Hofmann,A.
参考来源:AT 316542B; CH 502337
合成路线:The reaction of 4-hydroxy-2-methyl-indole (V) with 1-(N-benzylisopropylamino)-3-chloro-2-propanol (D) by means of NaOH in refluxing aqueous dioxane yields the corresponding benzylamine (X),which is debenzylated by catalytic hydrogenation.The reaction of 4-hydroxy-2-methyl-indole (V) with epichlorohydrin (A) and benzylamine (B) gives 4-(3-benzylamino-2-hydroxypropoxy)-2-methyl-indole (XI),which is debenzylated by hydrogenolysis to 4-(3-amino-2-hydroxypropoxy)-2-methyl-indole (XII).The condensation of (XII) with refluxing acetone (C) affords the corresponding N-isopropylidene derivative (XIII),which is finally hydrogenated with H2 over Pd/C in methanol.
参考文献标题:Verfahren zur Herstellung neuer Indolderivate
文献作者:Troxler,F.
参考来源:CH 472404; ES 337457
合成路线:4-Benzyloxy-indole-2-carboxylic acid (I) is converted into the corresponding dimethylamide (III),via the corresponding acid chloride (II); the dimethylamide (III) is reduced with LiAlH4 to give 4-benzyloxy-2-dimethylaminomethyl-indole (IV),which is hydrogenated to 4-hydroxy-2-methyl-indole (V).The reaction of (V) with epichlorohydrin (A) in aqueous NaOH gives the crude epoxide which without isolation is treated with isopropylamine (B) in refluxing dioxane.
参考文献标题:Verfahren zur Herstellung neuer Indolderivate
文献作者:Troxler,F.; Hofmann,A.
参考来源:CH 543505
合成路线:The reaction of 4-hydroxy-2-methyl-indole (V) with 1-(N-benzylisopropylamino)-3-chloro-2-propanol (D) by means of NaOH in refluxing aqueous dioxane yields the corresponding benzylamine (X),which is debenzylated by catalytic hydrogenation.The reaction of 4-hydroxy-2-methyl-indole (V) with epichlorohydrin (A) and benzylamine (B) gives 4-(3-benzylamino-2-hydroxypropoxy)-2-methyl-indole (XI),which is debenzylated by hydrogenolysis to 4-(3-amino-2-hydroxypropoxy)-2-methyl-indole (XII).The condensation of (XII) with refluxing acetone (C) affords the corresponding N-isopropylidene derivative (XIII),which is finally hydrogenated with H2 over Pd/C in methanol.
参考文献标题:Verfahren zur Herstellung von neuem 4-(2-Hydroxy-3-isopropylaminopropoxy)-2-methylindol und seiner S鋟readditionssalze Indolderivate
文献作者:Troxler,F.
参考来源:AT 317199
合成路线:The reaction of 4-hydroxy-2-methyl-indole (V) with 1-(N-benzylisopropylamino)-3-chloro-2-propanol (D) by means of NaOH in refluxing aqueous dioxane yields the corresponding benzylamine (X),which is debenzylated by catalytic hydrogenation.The reaction of 4-hydroxy-2-methyl-indole (V) with epichlorohydrin (A) and benzylamine (B) gives 4-(3-benzylamino-2-hydroxypropoxy)-2-methyl-indole (XI),which is debenzylated by hydrogenolysis to 4-(3-amino-2-hydroxypropoxy)-2-methyl-indole (XII).The condensation of (XII) with refluxing acetone (C) affords the corresponding N-isopropylidene derivative (XIII),which is finally hydrogenated with H2 over Pd/C in methanol.
参考文献标题:Verfahren zur Herstellung neuer Indolderivate
文献作者:Troxler,F.
参考来源:CH 469002; ES 337458
合成路线:4-Benzyloxy-indole-2-carboxylic acid (I) is converted into the corresponding dimethylamide (III),via the corresponding acid chloride (II); the dimethylamide (III) is reduced with LiAlH4 to give 4-benzyloxy-2-dimethylaminomethyl-indole (IV),which is hydrogenated to 4-hydroxy-2-methyl-indole (V).The reaction of (V) with epichlorohydrin (A) in aqueous NaOH gives the crude epoxide which without isolation is treated with isopropylamine (B) in refluxing dioxane.
合成路线:The reaction of 4-hydroxy-2-methyl-indole (V) with 1-(N-benzylisopropylamino)-3-chloro-2-propanol (D) by means of NaOH in refluxing aqueous dioxane yields the corresponding benzylamine (X),which is debenzylated by catalytic hydrogenation.The reaction of 4-hydroxy-2-methyl-indole (V) with epichlorohydrin (A) and benzylamine (B) gives 4-(3-benzylamino-2-hydroxypropoxy)-2-methyl-indole (XI),which is debenzylated by hydrogenolysis to 4-(3-amino-2-hydroxypropoxy)-2-methyl-indole (XII).The condensation of (XII) with refluxing acetone (C) affords the corresponding N-isopropylidene derivative (XIII),which is finally hydrogenated with H2 over Pd/C in methanol.
参考文献标题:Synthetic indoles.10.Chemistry of 4-hydroxy-indoles
文献作者:Seemann,F.; et al.
参考来源:Helv Chim Acta 1971,54(8),2411-19
产品链接: CAS No. 23694-81-7››