Acrylonitrile → HCID 11723894, compound

HRID 720401Notes

Reaction equation

HRID 720401 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:22]=[CH:21][C:7]([C:8](=[O:20])[CH2:9][N+:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.C(=O)(O)[O-].[Na+].[C:37](#[N:40])[CH:38]=[CH2:39]>CN(C)C=O>[C:37]([C:38]1[CH:39]=[C:9]([C:8](=[O:20])[C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:22][CH:21]=2)[N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:11]=12)#[N:40]

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 108082921-[2-(4-Methoxyphenyl)-2-oxoethyl]quinolin-1-ium bromide

Product 1

HCID 11723894HCID 11723894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-(4-methoxy-phenacyl)-quinolinium bromide (110 mg, 0.307 mmol), tetrapyridinecobalt(II) dichromate (202 mg, 0.332 mmol), sodium bicarbonate (66.2 mg, 0.788 mmol), acrylonitrile (110 μL, 1.67 mmol), and N,N-dimethylformamide (2.0 mL), similar to Example 1b, and yielded 26.6 mg (26%) as a yellow solid. 1H NMR (CDCl3): 8.08 (dd, J=9.15, 2.20 Hz, 2H), 8.02 (d, J=8.52 Hz, 1H), 7.83 (dd, J=7.55, 1.78 Hz, 1H), 7.70 (d, J=9.34 Hz, 1H), 7.66 (d, J=9.06 Hz, 1H), 7.59 (td, J=7.83, 1.83 Hz, 1H), 7.52 (td, J=7.48, 1.19 Hz, 1H), 7.38 (s, 1H), 7.05 (dd, J=9.25, 2.33 Hz, 2H), 3.94 (s, 3H).

Workup

  1. customyielded 26.6 mg (26%) as a yellow solid

Sources & evidence

ORD record
ord-625fc3192a9642f2a85a9405d2b830b9
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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