Acrylonitrile → HCID 86733852, compound

HRID 1283736Notes

Reaction equation

[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([C:14]1([OH:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:23])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1>>[C:1]([CH2:2][CH2:3][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)([OH:24])[C:15]1=[O:23])#[N:4]

Participants

Reactant 2

HCID 7855Acrylonitrile

HCID 31552531,3-Dihydro-3-hydroxy-3-[(3-methoxyphenyl)methyl]-2H-indol-2-one

Product 1

HCID 86733852HCID 86733852, compound

Procedure

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

Sources & evidence

ORD record: ord-903a99e4cb1a4006aae54864cce141b7
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03976645

Reaction notes

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