Acrylonitrile → HCID 15288586, compound

HRID 720398Notes

Reaction equation

HRID 720398 reaction equation
[Br-].[CH2:2]([N+:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.C(=O)(O)[O-].[Na+].[C:31](#[N:34])[CH:32]=[CH2:33]>CN(C)C=O>[C:3]([C:2]1[N:11]2[C:16]([CH:15]=[CH:14][CH:13]=[CH:12]2)=[C:32]([C:31]#[N:34])[CH:33]=1)(=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 27989541-(2-Oxo-2-phenylethyl)pyridin-1-ium bromide

Product 1

HCID 15288586HCID 15288586, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-(phenacyl)-pyridinium bromide (101 mg, 0.362 mmol), tetrapyridinecobalt(II) dichromate (246 mg, 0.403 mmol), sodium bicarbonate (84.9 mg, 1.01 mmol), acrylonitrile (120 μL, 1.82 mmol), and N,N-dimethylformamide (2.0 mL), similar to Example 1b, and yielded 30.5 mg (34%) as a white solid. 1H NMR (CDCl3): 9.96 (dd, J=6.05, 1.10 Hz, 1H), 7.82 (m, 3H), 7.61 (m, 2H), 7.52 (m, 3H), 7.17 (td, J=7.00, 1.29 Hz, 1H).

Workup

  1. customyielded 30.5 mg (34%) as a white solid

Sources & evidence

ORD record
ord-6b4a44bcbd5b455ca257dc93160c0d60
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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