Acrylonitrile → 1-(2-Cyanoethyl)-3-hydroxy-3-phenyl-indolin-2-one

HRID 1283732Notes

Reaction equation

HRID 1283732 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[OH:5][C:6]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][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]=[CH:18][CH:17]=2)[C:7]1=[O:15])#[N:4]

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 158063-Hydroxy-3-phenyl-1,3-dihydroindol-2-one

Product 1

HCID 215166441-(2-Cyanoethyl)-3-hydroxy-3-phenyl-indolin-2-one

Procedure

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

Sources & evidence

ORD record
ord-7ad8791147e34133aa7d1127af1983b5
Source dataset
uspto-grants-1976_08
Patent number
US03976645

Reaction notes

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