Acrylonitrile → HCID 10337357, compound

HRID 720404Notes

Reaction equation

HRID 720404 reaction equation
[Br-].[N+:2]([C:5]1[CH:23]=[CH:22][C:8]([C:9](=[O:21])[CH2:10][N+:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.C(=O)(O)[O-].[Na+].[C:38](#[N:41])[CH:39]=[CH2:40]>CN(C)C=O>[C:38]([C:39]1[CH:40]=[C:10]([C:9](=[O:21])[C:8]2[CH:22]=[CH:23][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][C:12]=12)#[N:41]

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 27811791-(4-nitrophenyl)-2-quinolinium-1-ylethan-1-one bromide

Product 1

HCID 10337357HCID 10337357, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-(4-nitro-phenacyl)-quinolinium bromide (119 mg, 0.319 mmol), tetrapyridinecobalt(II) dichromate (205 mg, 0.336 mmol), sodium bicarbonate (68.3 mg, 0.813 mmol), acrylonitrile (100 μL, 1.52 mmol), and N,N-dimethylformamide (2.0 mL), similar to Example 1b, and yielded 55.0 mg (50%) as a yellow solid. 1H NMR (CDCl3): 8.43 (dd, J=9.07, 2.20 Hz, 2H), 8.21 (dd, J=8.88, 2.13 Hz, 2H), 8.12 (d, J=8.52 Hz, 1H), 7.89 (dd, J=7.70, 1.64 Hz, 1H), 7.82 (d, J=9.07 Hz, 1H), 7.71 (d, J=9.06 Hz, 1H), 7.67 (ddd, J=8.17, 7.08, 1.58 Hz, 1H), 7.59 (td, J=7.49, 1.10 Hz, 1H), 7.44 (s, 1H).

Workup

  1. customyielded 55.0 mg (50%) as a yellow solid

Sources & evidence

ORD record
ord-61c379859735495aa523a4d403acf9d6
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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