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CAS No. : | 85633-41-6 | MDL No. : | MFCD11877750 |
Formula : | C12H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KVOMYFGYEIPWGE-UHFFFAOYSA-N |
M.W : | 199.21 | Pubchem ID : | 13365800 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | |
Hazard Statements: | H302-H312-H332 | Packing Group: | |
GHS Pictogram: |
* 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 water; trifluoroacetic acid 1.) 80 deg C, 4 h, 2.) RT, 20 min; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With perhydrodibenzo-18-crown-6; sodium hydride In toluene for 48h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) NaNO2, conc H2SO4, 2.) H2O / 1.) water, 1 h, 2.) 160 deg C, 10 min 2: 1.) trifluoroacetic acid, 2.) water / 1.) 80 deg C, 4 h, 2.) RT, 20 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 61 percent / NaH, dicyclohexyl-18-crown-6 / toluene / 48 h / Ambient temperature 2: 0.1N aq. NaOH / methanol / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With mono(N,N,N-trimethylbenzenaminium) tribromide In methanol; dichloromethane at 20℃; for 2h; | 3; 20.20-a Scheme 3; Preparation of 5-(pyridin-3-yl)benzofuran derivatives; Preparation of 4-[amino-(5-pyridin-3-yl-benzofuran-2-yl)-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile compounds; Example 20; Preparation of 4-[amino-[7-(3-fluoro-phenyl)-5-pyridin-3-yl-benzofuran-2-yl]-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile; 20-a) Preparation of 3-bromo-2-hydroxy-5-pyridine-3-yl- benzaldehyde To a solution of 2-hydroxy-5-pyridine-3-yl-benzaldehyde (20.0 g, 100 mmol) in DCM/MeOH (500/200 ml) was added benzyltrimethylammonium tribrommide (39.1 g, 100 mmol) at room temperature. After stirring at room temperature for 2h, the mixture was quenched with water. The mixture was extracted with DCM (* 2). The organic layers were combined, dried over MgS04, filtered and evaporated in vacuo to give 25.0 g of 3-bromo-2-hydroxy-5-pyridine-3-yl-benzaldehyde as a light yellow solid (crude). LCMS (condition B) m/z 278 [M+H] +, retention time 2.54 minutes ; 1H-NMR (CDCl3) δ 11.65 (s, 1H), 9.96 (s, 1H), 8.83 (d, J= 1.7 Hz, 1H), 8.64 (dd, J= 1.7, 4.8 Hz, 1H), 8.03 (d, J= 2.3 Hz, 1H), 7.86 (ddd, J= 1.7, 2.3, 7.9 Hz, 1H), 7.76 (d, J= 2.3 Hz, 1H), 7.41 (dd, J= 4.8, 7.9 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | 31 5-(3-Pyridyl)salicylaldehyde thiosemicarbazone Example 31 5-(3-Pyridyl)salicylaldehyde thiosemicarbazone The 5-(3-pyridyl)salicylaldehyde_was obtained in a yield of 40% according to General Procedure B using 3-pyridyl boronic acid and 5-bromo salicylaldehyde as starting matrial. The title compound is made from 5-(3-pyridyl)salicylaldehyde and thiosemi-carbazide, using General Procedure A. 1H NMR (d6-DMSO) δ7.01 (d, 1H), 7.45 (t, 1H), 7.53 (d, 1H), 8.08 (d, 1H), 8.18 (d, 1H), 8.22 (s, 1H), 8.32 (s, 1H), 8.42 (s, 1H), 8.53 (s, 1H), 8.95 (s, 1H), 10.25 (s, 1H), 11.42 (s, 1H). MS 273 (M+H), C13H12N4OS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | ||
23 2-Formyl-4-(3-pyridyl)phenol An additional recrystallization from acetone-hexane gives an analytical sample of the titled product as very pale yellow crystals with a melting point of 123°-124° C. The IR (Nujol) spectrum reveals peaks at 2567, 1674, 1608, 1308, 1290, 1259, 1241, 1196, 1166, 1117, 1034, and 810 cm-1. The NMR (CDCl3, δ) spectrum reveals peaks at 10.03, 8.86, 8.64, and 7.95-7.05. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With piperidine In acetonitrile at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 20 - 80℃; for 2.3h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With K2CO3 In dimethyl sulfoxide react. Pt complex, aldehyde, amine and K2CO3 in DMSO at 150°C for2 h, cooling; centrifugation, washing ppt. with water, methanol; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With K2CO3 In dimethyl sulfoxide react. Pt complex, aldehyde, amine and K2CO3 in DMSO at 150°C for2-4 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With K2CO3 In dimethyl sulfoxide react. Pt complex, aldehyde, amine and K2CO3 in DMSO at 150°C for2-4 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With K2CO3 In dimethyl sulfoxide react. Pt complex, aldehyde, amine and K2CO3 in DMSO at 150°C for2-4 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In ethanol for 18h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In ethanol for 15h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In ethanol for 17h; Reflux; | |
In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol for 4h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: K2CO3 / dimethyl sulfoxide 2: chloroform |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In tetrahydrofuran; ethanol for 10h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In ethanol for 15h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In ethanol for 2h; Reflux; |
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