Acrylonitrile → HCID 21516627, compound

HRID 1283735Notes

Reaction equation

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

Participants

Reactant 2

HCID 7855Acrylonitrile

HCID 21537963HCID 21537963, compound

Product 1

HCID 21516627HCID 21516627, compound

Procedure

Reaction of acrylonitrile with 3 -(m-fluorophenyl)- 3-hydroxyindolin-2-one by a procedure analogous to that of Example 1 gives 1-(2-cyanoethyl)- 3-(m-fluorophenyl)- 3-hydroxyindolin-2-one. Hydrogenation of 1-(2-cyanoethyl)- 3-(m-fluorophenyl)-3-hydroxyindolin-2-one by a procedure analogous to that of Example 2 gives 1-(3-aminopropyl)- 3-(m-fluorophenyl)-3-hydroxyindolin-2-one. Cyclodehydration of 1-(3-aminopropyl)-3-(m-fluorophenyl)-3-hydroxyindolin-2-one by a procedure analogous to that of Example 3 gives 10-(m-fluorophenyl)- 2,3,4,10-tetrahydropyrimido[ 1,2-a] indol-10-ol.

Sources & evidence

ORD record: ord-22f1350b0caa4fd5abae2f638572ee02
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03976645

Reaction notes

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