Acrylonitrile → HCID 10470636, compound

HRID 720406Notes

Reaction equation

HRID 720406 reaction equation
[Br-].[CH3:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N+:6]([CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])=[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:14]([C:13]1[N:6]2[C:7]3[C:12]([C:3]([CH3:2])=[CH:4][C:5]2=[C:37]([C:36]#[N:39])[CH:38]=1)=[CH:11][CH:10]=[CH:9][CH:8]=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 2841258HCID 2841258, compound

Product 1

HCID 10470636HCID 10470636, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 4-methyl-1-phenacyl-quinolinium bromide (86.5 mg, 0.253 mmol), tetrapyridinecobalt(II) dichromate (163 mg, 0.263 mmol), sodium bicarbonate (53.6 mg, 0.638 mmol), acrylonitrile (100 μL, 1.52 mmol), and N,N-dimethylformamide (2.0 mL), similar to Example 1b, and yielded 30.0 mg (38%) as a yellow solid. 1H NMR (CDCl3): 8.12 (m, 1H), 8.06 (m, 2H), 7.98 (m, 1H), 7.69 (tt, J=7.37, 1.56 Hz, 1H), 7.53–7.64 (m, 5H) 7.38 (s, 1H), 2.72 (d, J=1.10 Hz, 3H).

Workup

  1. customyielded 30.0 mg (38%) as a yellow solid

Sources & evidence

ORD record
ord-421f0bd801b542c0b756bea990e6469e
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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