Quinoline → HCID 9971844, compound

HRID 720409Notes

Reaction equation

HRID 720409 reaction equation
[NH+:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.C(=O)(O)[O-:31].[Na+].[C:35](#[N:38])C=C>CN(C)C=O>[C:35]([C:19]1[CH:18]=[C:17]([C:16]([C:15]2[CH:20]=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:31])[N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][C:2]=12)#[N:38]

Participants

7

Reactant 5

HCID 7047QuinolineHCID 7855AcrylonitrileHCID 24503Dichromate ionHCID 516892Sodium BicarbonateHCID 4992033Quinolinium

Product 1

HCID 9971844HCID 9971844, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The quinolinium salt/quinoline mixture was prepared from 3-acetyl-pyridine (440 μL, 4.00 mmol), quinoline (5.0 mL, 42 mmol) and iodine (1.02 g, 4.00 mmol) similar to Example 14, and yielded 312 mg of a brownish-green solid. The title compound was prepared from the quinolinium salt/quinoline mixture (290 mg), tetrapyridinecobalt(II) dichromate (346 mg, 0.568 mmol), sodium bicarbonate (131 mg, 1.56 mmol), acrylonitrile (180 μL, 2.73 mmol), and N,N-dimethylformamide (2.0 mL) similar to Example 14, yielded 15.5 mg (1.3% over 2 steps) as a yellow solid. 1H NMR (CDCl3): 8.80 (ddd, J=4.12, 1.65, 0.96 Hz, 1H), 8.24 (d, J=7.97 Hz, 1H), 8.12 (d, J=8.52 Hz, 1H), 7.99 (td, J=7.76, 1.83 Hz, 1H), 7.85 (m, 2H), 7.76 (d, J=9.07 Hz, 1H), 7.69 (d, J=9.06 Hz, 1H), 7.52–7.65 (m, 3H).

Workup

  1. customyielded 15.5 mg (1.3% over 2 steps) as a yellow solid

Sources & evidence

ORD record
ord-67335059ddfa49bd914b2aab7f6f203f
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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