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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Quinoline-2-carboxaldehyde is a quinoline compound with various biological activities, used as a fluorescent probe, catalyst, or organic synthesis precursor. Its structural features allow it to react with amines to form Schiff bases, used for labeling proteins, enzymes, and other biomolecules.
Synonyms: 2-Quinolinecarboxaldehyde
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CAS No. : | 5470-96-2 |
Formula : | C10H7NO |
M.W : | 157.17 |
SMILES Code : | O=CC1=NC2=CC=CC=C2C=C1 |
Synonyms : |
2-Quinolinecarboxaldehyde
|
MDL No. : | MFCD00075032 |
InChI Key : | WPYJKGWLDJECQD-UHFFFAOYSA-N |
Pubchem ID : | 79619 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; In methanol; for 3h;Reflux; | A mixture of quinoline-2-carboxaldehyde (1 .57 g; 0.01 mol) and 2-(3,4,5-trimethoxyphenyl) acetonitrile (2.07 g; 0.01 mol), sodium methoxide (1 .0 gm) in methanol (50 ml) were stirred at reflux temperature for 3 hours. The reaction mass was cooled to room temperature, and crushed ice was added to get a solid product. The crude solid was separated by filtration and washed several times with cold methanol (3x5 ml). The isolated yellow solid was recrystallized from methanol and gave (Z)-3-(quinolin-2-yl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile as a yellow fluffy product. MF:C21H18N203, mp:106-10&C, 1H NMR (400 MHz, CDCI3): 63.91 (s, 3H), 3.96 (s, 6H),7.02 (s, 2H), 7.61 (t, 1H, J1=7.6 Hz, J2=14.8 Hz), 7.78-7.79 (d, 1H, J=7.2 Hz), 7.86 (s,1H), 7.86-7.88 (d, 1H, J=8.40 Hz), 8.14-8.20 (m, 2H), 8.27-8.29 (d, 1H, J=8.8 Hz) ppm;130 NMR (100 MHz, CDCI3): 6 56.29, 60.96, 103.74, 115.91, 117.44, 120.54, 127.55,127.64, 127.73, 127.86, 129.43, 129.60, 130.35, 137.00, 139.73, 140.74, 140.87,148.10, 152.21, 153.59 ppm. | |
With sodium methylate; In methanol; at 20℃; | General procedure: In the first synthetic step (step a, Scheme 1), a series of (Z)-substituted diarylacrylonitrile analogues were synthesized by reacting substituted benzyl carbaldehydes with their corresponding substituted phenylacetonitriles in 5% NaOMe in methanol. The reaction mixture was stirred at room temperature for 2-3 h for the reaction to complete and the final product precipitated of the solution. The precipitate was filtered, washed with water and dried to yield the final compound in yields ranging from 70 to 95% (Scheme 1) [16]. |