Acrylonitrile → HCID 11724229, compound

HRID 720402Notes

Reaction equation

HRID 720402 reaction equation
[Br-].[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7](=[O:19])[CH2:8][N+:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.C(=O)(O)[O-].[Na+].[C:36](#[N:39])[CH:37]=[CH2:38]>CN(C)C=O>[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:8]2[N:9]3[C:18]4[C:13]([CH:12]=[CH:11][C:10]3=[C:37]([C:36]#[N:39])[CH:38]=2)=[CH:14][CH:15]=[CH:16][CH:17]=4)=[O:19])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 10713707N-(4'-Chlorophenacetyl) quinoline bromide salt

Product 1

HCID 11724229HCID 11724229, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-(4-chloro-phenacyl)-quinolinium bromide (82.3 mg, 0.227 mmol), tetrapyridinecobalt(II) dichromate (151 mg, 0.248 mmol), sodium bicarbonate (49.5 mg, 0.589 mmol), acrylonitrile (100 μL, 1.52 mmol), and N,N-dimethylformamide (2.0 mL), similar to Example 1b, and yielded 15.6 mg (20%) as a yellow solid. 1H NMR (CDCl3): 8.03 (m, 3H), 7.86 (dd, J=7.97, 1.64 Hz, 1H), 7.75 (d, J=9.34 Hz, 1H), 7.68 (d, J=9.34 Hz, 1H), 7.62 (ddd, J=8.31, 7.07, 1.72 Hz, 1H), 7.55 (m, 3H), 7.41 (s, 1H).

Workup

  1. customyielded 15.6 mg (20%) as a yellow solid

Sources & evidence

ORD record
ord-0edc572500584414ba85353be0663d83
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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