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CAS No. : | 24964-64-5 | MDL No. : | MFCD00003344 |
Formula : | C8H5NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HGZJJKZPPMFIBU-UHFFFAOYSA-N |
M.W : | 131.13 | Pubchem ID : | 90670 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
81% | General procedure: 3-Cyanobenzaldehyde (11a) or 4-cyanobenzaldehyde (11b) (15 mmol) and malonic acid (30 mmol) were dissolved in pyridine (30 mL). Piperidine (3.0 mmol) was added and the reaction was heated for 4 h at 100 C. The reaction was cooled to room temperature and 5 M HCl (25 mL) was added slowly. The resulting white precipitate was collected by filtration, washed with water and dried to give (E)-3-cyanocinnamic acid (12a) or (E)-4-cyanocinnamic acid (12b) in yields of 81% and 78%, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; at -78℃; for 0.5h; | To a solution of <strong>[197007-87-7](4-bromo-pyridin-3-yl)-methanol</strong> (53 mg 0.2 mmol) in THF (2 ml_) at -78C was added dropwise 2.5 M n-butyllithium (0.24 mL, 0.6 mmol). After 15 min a solution of 3-cyanobenzaldehyde (79 mg) in THF (0.5 ml) was added. The reaction mixture was stirred for 15 min, then quenched with ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and the residue purified by flash chromatography to yield 3-{hydroxy-[3-(hydroxy-phenyl-methyl)-pyridin-4- yl]-methyl}-benzonitrile as white crystals.LCMS: 2.250 min, m/z: 317 (M + 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; at -78℃; for 0.5h; | To a solution of <strong>[197007-87-7](4-bromo-pyridin-3-yl)-methanol</strong> (20 mg, 0.11 mmol) inTHF (1 ml_) at -78C was added dropwise 2. 5M ?-butyllithium (0.22 ml_). After 15 min, a solution of 3-cyanobenzaldehyde (69 mg) in THF (0.5 ml_) was added. The reaction mixture was stirred for 15 min, then quenched with ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography to yield 3-[hydroxy-(3-hydroxymethyl-pyridin-4-yl)- methyl]-benzonitrile as a white solid. | |
With n-butyllithium; In tetrahydrofuran; at -78℃; for 0.5h; | To a solution of <strong>[197007-87-7](4-bromo-pyridin-3-yl)-methanol</strong> (20 mg, 0.11 mmol) inTHF (1 mL) at -78C was added dropwise 2. 5M n-butyllithium (0.22 mL). After 15 min, a solution of 3-cyanobenzaldehyde (69 mg) in THF (0.5 mL) was added. The reaction mixture was stirred for 15 min, then quenched with ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography to yield 3-[hydroxy-(3-hydroxymethyl-pyridin-4-y|)- methyl]-benzonitrile as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With hydrogenchloride; In hexane; ethyl acetate; toluene; | A. Preparation of tert-butyl 2-methoxycarbonyl-3-(3-cyanophenyl)-acrylate. To a solution of 3-cyanobenzaldehyde (0.700 g, 5.34 mmol) and t-butyl methyl malonate (0.845 mL, 5.00 mmol) in toluene (40 mL), piperidine (0.500 mL, 5.06 mmol) was added. The mixture was heated to reflux overnight. Dean-Stark apparatus was used to remove generated water. Ethyl acetate (50 mL) and 0.5 N HCl (50 mL) were added. Organic phase was separated, washed with saturated aq. NaHCO3, dried over Na2SO4, concentrated in vacuo to give an oil. The oil was dry-packed onto a silica gel column, eluted with hexane first, then with 5percent to 10percent EtOAc in hexane gradually to give the desired product as a mixture of E and Z isomers (0.44 g) (yield: 31percent). 1H NMR (CDCl3) 7.78-7.57 (m, 3H), 7.57-7.43 (m, 1H), 3.88 (s, 3H, minor isomer), 3.85 (s, 3H, major isomer), 1.53 (br. s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With malonic acid; | (a) 3-Cyanocinnamic acid 3-Cyanobenzaldehyde was reacted with malonic acid by the method described in Example 2(a) to give the title product, m.p. ca 240 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 229 3-(3-Cyano-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-cyanobenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 172-174 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | General procedure: All materials were dried for one day at 120 C. Chloride and carbonyl derivatives were introduced into a Schlenk of 30 mL. Products were put in vacuo, then under nitrogen. An appropriate volume of anhydrous DMF was added after 10 min of nitrogen bubbling. The solution was vigorously stirred for 20 min at -20 C. TDAE was added slowly under inert atmosphere. The reaction was stirred for one hour. The second reaction phase was performed at rt or at temperature according to procedure of synthesis. The reaction was hydrolysed with distilled water after TLC analysis clearly showed that the chloride 1 had been totally consumed. The aqueous solution was extracted with dichloromethane and the combined organic layers washed with brine then dried on MgSO4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.8% | To the reactor was added 100 mmol of the compound of formula (I), 500 ml of benzene and 180 mmolSilver acetate,Then stir and mixAdd 5-10 minutes, continue to stir by adding 10mmol1-cyanopropyl-3-methylimidazolium tetrafluoroborate and120 mmolO-nitrobenzoic acid,After the addition, the mixture was heated to 80 C and stirred for 8 hours.After completion of the reaction, the reaction system was allowed to cool to room temperature, and then the solvent was removed under reduced pressure. The residue was passed through a silica gel columnChromatographic separation in which a mixed solution of acetone and n-hexane in a volume ratio of 1: 2 was used as an eluent to give a compound of formula (I)And the yield was 94.8% |