Acrylonitrile → HCID 21446967, compound

HRID 597185Notes

Reaction equation

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

Participants

Reactant 2

HCID 7855Acrylonitrile

HCID 148928851,4-Bis(trimethylsilyl)-1,4-dihydroquinoline

Product 1

HCID 21446967HCID 21446967, compoundYield 73.6%

Conditions

Temperature: 100 °C

Procedure

A mixture consisting of 27.5 g (0.1 mol) of 1,4-bis-(trimethylsilyl)-1,4-dihydroquinoline and 6 g (0.1 mol) of acrylonitrile is heated in an inert atmosphere at 100°C for 150 hours. Fractional distillation yields 24.2 g (72%) of 1,4-bis-(trimethylsilyl)-2-(1-cyanoethyl)-1,2-dihydroquinoline: yellow-green oil, b.p. 106°-108°C/0.001 mm.

Workup

distillationFractional distillation

Sources & evidence

ORD record: ord-347bc777635c473eb50aeb21ca8c40b9
Source dataset: uspto-grants-1977_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04013661

Reaction notes

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