Acrylonitrile → HCID 21516640, compound

HRID 1283733Notes

Reaction equation

[C:1](#[N:4])[CH:2]=[CH2:3].[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[C:9]2([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[OH:16]>>[Cl:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:3][CH2:2][C:1]#[N:4])[C:10](=[O:15])[C:9]2([OH:16])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Reactant 2

HCID 7855Acrylonitrile

HCID 12862128HCID 12862128, compound

Product 1

HCID 21516640HCID 21516640, compound

Procedure

Reaction of acrylonitrile with 5-chloro-3-phenyl-3-hydroxyindolin-2-one by a process analogous to that of Example 1 gives 5-chloro-1-(cyanoethyl)-3-hydroxy-3-phenylindolin-2-one. Hydrogenation of the 5-chloro-1-(2-cyanoethyl)-3-hydroxy-3-phenylindolin-2-one by a procedure analogous to that of Example 2 gives 1-(3-aminopropyl)-5-chloro-3-hydroxy-3-phenylindolin-2-one. Cyclodehydration of the 1-(3-aminopropyl)-5-chloro-3-hydroxy-3-phenylindolin-2-one by a procedure analogous to that of Example 3 gives 8-chloro-2,3,4,10-tetrahydro-10-phenylpyrimido [1,2-a] indol-10 -ol.

Sources & evidence

ORD record: ord-747482f59f60431fbc0cc6ad1321363b
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03976645

Reaction notes

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