Acrylonitrile → HCID 10425502, compound

HRID 720400Notes

Reaction equation

HRID 720400 reaction equation
[Br-].[CH3:2][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>[C:36]([C:37]1[CH:38]=[C:8]([C:7](=[O:19])[C:6]2[CH:5]=[CH:4][C:3]([CH3:2])=[CH:21][CH:20]=2)[N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]=12)#[N:39]

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 10807217HCID 10807217, compound

Product 1

HCID 10425502HCID 10425502, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-(4-methyl-phenacyl)-quinolinium bromide (120 mg, 0.350 mmol), tetrapyridinecobalt(II) dichromate (229 mg, 0.376 mmol), sodium bicarbonate (74.7 mg, 0.889 mmol), acrylonitrile (120 μL, 1.82 mmol), and N,N-dimethylformamide (2.5 mL), similar to Example 1b, and yielded 30.6 mg (28%) as a yellow solid. 1H NMR (CDCl3): 8.05 (d, J=8.51 Hz, 1H), 7.98 (dd, J=6.60, 1.65 Hz, 2H), 7.84 (dd, J=7.83, 1.51 Hz, 1H), 7.71 (d, J=9.34 Hz, 1H), 7.67 (d, J=9.07 Hz, 1H), 7.60 (ddd, J=8.24, 7.08, 1.58 Hz, 1H), 7.52 (td, J=7.49, 1.19 Hz, 1H), 7.40 (s, 1H), 7.37 (d, J=7.97 Hz, 2H), 2.50 (s, 3H).

Workup

  1. customyielded 30.6 mg (28%) as a yellow solid

Sources & evidence

ORD record
ord-12f61d025f934338ae84fa864fa497da
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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