Acrylonitrile → HCID 21516634, compound

HRID 1283737Notes

Reaction equation

[C:1](#[N:4])[CH:2]=[CH2:3].[OH:5][C:6]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=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:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:7]1=[O:15])#[N:4]

Participants

Reactant 2

HCID 7855Acrylonitrile

HCID 21516639HCID 21516639, compound

Product 1

HCID 21516634HCID 21516634, compound

Procedure

Reaction of acrylonitrile with 3-hydroxy-3-(m-trifluoromethylphenyl)-indolin-2-one by a process analogous to that of Example 1 gives 1-(2-cyanoethyl)-3-hydroxy-3-(m-trifluoromethylphenyl)indolin-2-one. Hydrogenation of the 1-(2-cyanoethyl)-3-hydroxy-3-(m-trifluoromethylphenyl)indolin-2-one gives 1-(3-aminopropyl)-3-hydroxy-3-(m-trifluoromethylphenyl)indolin-2-one. Cyclodehydration of 1-(3-aminopropyl)-3-hydroxy-3-(m-trifluoromethylphenyl)indolin-2-one by a procedure analogous to that of Example 3 gives 10-(m-trifluoromethylphenyl)-2,3,5,10-tetrahydropyrimido [1,2-a] indol-10-ol.

Sources & evidence

ORD record: ord-520aa26ed8e04223a2637be48cd87c43
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03976645

Reaction notes

Loading…