Acrylonitrile → HCID 10022323, compound

HRID 720399Notes

Reaction equation

HRID 720399 reaction equation
[Br-].[Br:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6](=[O:18])[CH2:7][N+:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=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>[Br:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6]([C:7]1[N:8]2[C:17]3[C:12]([CH:11]=[CH:10][C:9]2=[C:37]([C:36]#[N:39])[CH:38]=1)=[CH:13][CH:14]=[CH:15][CH:16]=3)=[O:18]

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 21892166HCID 21892166, compound

Product 1

HCID 10022323HCID 10022323, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 1-(3-bromo-phenacyl)-quinolinium bromide (150 mg, 0.368 mmol), tetrapyridinecobalt(II) dichromate (306 mg, 0.502 mmol), sodium bicarbonate (96.3 mg, 1.15 mmol), acrylonitrile (150 μL, 2.28 mmol), and N,N-dimethylformamide (4.0 mL), similar to Example 1b, and yielded 21.2 mg (15%) as a yellow solid. 1H NMR (CDCl3): 8.20 (t, J=1.79 Hz, 1H), 8.06 (d, J=8.51 Hz, 1H), 7.98 (dt, J=6.25, 1.38 Hz, 1H), 7.86 (dd, J=7.83, 1.51 Hz, 1H), 7.81 (ddd, J=6.52, 2.06, 0.96 Hz, 1H), 7.76 (d, J=9.06 Hz, 1H), 7.69 (d, J=9.06 Hz, 1H), 7.63 (ddd, J=8.31, 7.14, 1.65 Hz, 1H), 7.56 (td, J=7.41, 1.10 Hz, 1H), 7.45 (t, J=7.83 Hz, 1H), 7.44 (s, 1H).

Workup

  1. customyielded 21.2 mg (15%) as a yellow solid

Sources & evidence

ORD record
ord-54fc46efc60d4d139327102eb6e7964c
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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