Acrylonitrile → HCID 10448103, compound

HRID 720407Notes

Reaction equation

HRID 720407 reaction equation
[Br-].[CH3:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N+:9]([CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])=[CH:8][CH:7]=[CH:6]2.[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:14]([C:13]1[N:9]2[C:10]3[C:5]([CH:6]=[CH:7][C:8]2=[C:37]([C:36]#[N:39])[CH:38]=1)=[CH:4][C:3]([CH3:2])=[CH:12][CH:11]=3)(=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 2826943HCID 2826943, compound

Product 1

HCID 10448103HCID 10448103, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 6-methyl-1-phenacyl-quinolinium bromide (103 mg, 0.300 mmol), tetrapyridinecobalt(II) dichromate (193 mg, 0.317 mmol), sodium bicarbonate (63.4 mg, 0.755 mmol), acrylonitrile (100 μL, 1.52 mmol), and N,N-dimethylformamide (2.0 mL), similar to Example 1b, and yielded 40.2 mg (43%) as a yellow solid. 1H NMR (CDCl3): 8.06 (m, 2H), 7.98 (d, J=8.76 Hz, 1H), 7.62–7.71 (m, 4H), 7.57 (t, J=7.56 Hz, 2H), 7.42 (m, 2H), 2.51 (s, 3H).

Workup

  1. customyielded 40.2 mg (43%) as a yellow solid

Sources & evidence

ORD record
ord-2351e26436eb4148a6df8e96fee8593a
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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