Acrylonitrile → HCID 21516636, compound

HRID 1283734Notes

Reaction equation

[C:1](#[N:4])[CH:2]=[CH2:3].[OH:5][C:6]1([C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:15]>>[C:1]([CH2:2][CH2:3][N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([OH:5])([C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[C:7]1=[O:15])#[N:4]

Participants

Reactant 2

HCID 7855Acrylonitrile

HCID 21516628HCID 21516628, compound

Product 1

HCID 21516636HCID 21516636, compound

Procedure

Reaction of acrylonitrile with 3-hydroxy-3-(m-tolyl)indolin- 2-one by a procedure analogous to that of Example 1 gives 1-(2-cyanoethyl)- 3-hydroxy-3-(m-tolyl)indole- 2-one. Hydrogenation of 1-(2-cyanoethyl)-3-hydroxy-3-(m-tolyl) indolin-2-one by a procedure analogous to that of Example 2 gives 1-(3-aminopropyl)-3-hydroxy-3-(m-tolyl)indolin- 2-one. Cyclodehydration of 1-(3-aminopropyl)-3-hydroxy-3-(m-tolyl) indolin -2-one by a procedure analogous to that of Example 3 gives 2,3,4,10-tetrahydro-10-(m-tolyl) pyrimido[ 1,2-a] indol-10-ol.

Sources & evidence

ORD record: ord-146df67ae474479f8d6f7627fd229cdd
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03976645

Reaction notes

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