1H-indol-4-ol → 4-hydroxy-1H-indole-3-carbonitrile

HRID 648727Notes

Reaction equation

HRID 648727 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH:11][C:12]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2>>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:15]#[N:16])=[CH:5][NH:6]2.[OH:11][C:12]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]2[C:13]=1[C:14]([C:5]#[N:6])=[CH:15][NH:16]2

Participants

4

Reactant 2

HCID 754211H-indol-4-olHCID 199676646-Methyl-1H-indol-4-ol

Product 2

HCID 131869494-hydroxy-1H-indole-3-carbonitrileHCID 21243577HCID 21243577, compound

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-methylindole, 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 Germany 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 Germany Patent Specification No. 30 30 047).

Sources & evidence

ORD record
ord-d52f21fdd0cc4fe2b0eb88bcdc21d196
Source dataset
uspto-grants-1988_04
Patent number
US04736043

Reaction notes

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