Indole-5-carbonitrile → 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

HRID 2404952Notes

Reaction equation

HRID 2404952 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[NH:9][CH:8]=1)[OH:6].N1C2C(=CC(C#N)=CC=2)C=C1.ClCCCC(Cl)=O>>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[NH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 3

HCID 27513Indole-5-carbonitrileHCID 783704-Chlorobutyryl chlorideHCID 71714930HCID 71714930, compound

Product 1

HCID 102205283-(4-chlorobutanoyl)-1H-indole-5-carbonitrile

Procedure

In the second reaction line is schematically illustrated the synthesis of the intermediate 3-(4-chloro-1-hydroxy-butyl)-1H-indol-5-carbonitrile of Formula (I) through the condensing of indol-5-carbonitrile with 4-chlorobutyrylchloride to give 3-(4-chlorobutyryl)-1H-indol-5-carbonitrile, which is reduced with sodium borohydride, to give 3-(4-chloro-1-hydroxy-butyl)-1H-indol-5-carbonitrile.

Sources & evidence

ORD record
ord-6eb83bb228ab4d3d91d73de9d241ef49
Source dataset
uspto-grants-2014_08
Patent number
US08802851B2

Reaction notes

Loading…