HCID 12798005, compound → HCID 21243579, compound
Reaction equation
OC1C=CC=C2C=1C(C#N)=CN2.[O:13]1[CH2:28][CH:14]1[CH2:15][O:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[C:19]([C:26]#[N:27])=[CH:20][NH:21]2.[CH2:29]([O:32][C:33]1[CH:42]=[CH:41][CH:40]=[CH:39][C:34]=1[O:35][CH2:36][CH2:37][NH2:38])[CH:30]=[CH2:31]>>[OH:13][CH:14]([CH2:28][NH:38][CH2:37][CH2:36][O:35][C:34]1[CH:39]=[CH:40][CH:41]=[CH:42][C:33]=1[O:32][CH2:29][CH:30]=[CH2:31])[CH2:15][O:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[C:19]([C:26]#[N:27])=[CH:20][NH:21]2Participants
Procedure
Compounds of general formula (I) can be further reacted by known methods, for example by saponification and decarboxylation to give 4-hydroxyindole or 4-hydroxy-6-methylindole, or by aminolysis and dehydration to give 4-hydroxy-3-cyanoindole or 4-hydroxy-3-cyano-6-methyl-indole, which, by reaction with epichlorohydrin and alkylamino derivatives, give aminopropanols with useful pharmacological properties (see Federal Republic of Germany Patent Specification Nos. 25 08 251; 27 37 630; 29 05 877 and 30 30 047). However, compounds of general formula (I) can also be reacted to give aminopropanol derivatives directly, whereafter the compounds obtained are subsequently changed. Thus, for example, from 4-hydroxy-3-cyanoindole (see Federal Republic of German Patent Specification No. 30 29 980) there is obtained 4-(2,3-epoxypropoxy)-3-cyanoindole which is reacted with 2-(2-allyloxyphenoxy)-ethylamine to give the pharmacologically effective 4-{2-hydroxy-3-[2-(2-allyloxyphenoxy)-ethylamino]-propoxy}-3-cyanoindole (see Example 3h) of Federal Republic of German Patent Specification No. 30 30 047).
Workup
- customwhereafter the compounds obtained
Sources & evidence
- ORD record
- ord-252d98420e03413eb1f3ae458ba758c7
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04824965
Reaction notes
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