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CAS No. : | 2215-77-2 | MDL No. : | MFCD00002539 |
Formula : | C13H10O3 | Boiling Point : | - |
Linear Structure Formula : | C6H5OC6H4COOH | InChI Key : | RYAQFHLUEMJOMF-UHFFFAOYSA-N |
M.W : | 214.22 | Pubchem ID : | 75182 |
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 |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 2.0h; | To a stirred solution of 3-cyanobenzaldeliyde (3.25 mmol) was added iV-metliyl piperizine (3.25 mmol) followed by NaB(OAc)3H (4.25 (mmol). The mixture was stirred for 4 h and concentrated. The residual material was partitioned between CH2Cl2 and NaHCC>3 (sat.) and the organic phase was then collected. The organic phase was concentrated (0.70 g, 3.25 mmol) and dissolved in THF (5 mL). The solution was cooled in an ice bath, and to this was added lithium aluminum hydride (1.0 M in THF, 4.8 mL, 4.88 mmol). The solution was warmed to room temperature and stirred for 2 h. The reaction was quenched with excess sodium sulfate decahydrate (~1 g), and then filtered through diatomaceous earth. The material was concentrated to give a clear oil of the benzylamine which was used without further purification. 4-Phenoxy benzoic acid was dissolved in CH2Cl2 (2 mL) and to titiis was added EDCI (0.107 g, 0.56 mmol) followed by DIEA (0.048 mL, 0.56 mmol) and the benzyl amine obtained from the previous step (0.10 g, 0.50 mmol). The reaction was stirred for 2 h, and then partitioned between CH2Cl2 and NaHCO3 (sat.). The organic layer was concentrated and the residual oil chromatographed (SiO2, CH2Cl2/5% NH3 in MeOH, 95:5) to give the title compound as a white solid.1HNMR (CDCl3, 300 MHz) delta 2.30 (s, 3H), 2.49 (br s, 8H), 3.51 (s, 2H), 4.63 (d, 2H, J = 5.4 Hz), 6.27 (s, IH), 6.96-7.05 (m, 4H), 7.16 (t, IH, J = 7.5 Hz), 7.25 (m, IH), 7.30-7.39 (m, 5H), 7.75-7.78 (d, 2H, J = 7.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With aluminum (III) chloride; at 200℃; for 3h;Inert atmosphere; | General procedure: In a 10 mL round-bottomed flask, (phenylsulfonyl)acetonitrile (544mg, 3.0 mmol, 1.0 equiv) was added to a mixture of acid 1(3.0mmol) and AlCl3(8 mg, 0.06 mmol, 0.02 equiv). The mixture was then stirred under argon at 200 C for 3 h. After completion of the reaction, the crude mixture was diluted with CH2Cl2(5 mL + 5 mL),silica gel (3 g) was then added to make a solid deposit after evaporation of the solvent. A silica gel column chromatography (eluent:PE-EtOAc, 95:5) finally afforded the pure nitrile together with methyl phenyl sulfone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With aluminum (III) chloride; at 200℃; for 5h;Sealed tube; | General procedure: In a glass tube, the glutaronitrile (282 mg, 3.0 mmol, 1.0 equiv) wasadded to a mixture ofthe respective acid 1(3.0 mmol) and AlCl3(8mg, 0.06 mmol, 0.02 equiv). The tubewas then sealed (with a screwcap) and the mixture was allowed to stir at 200 C for 5 h. Aftercompletion of the reaction, the crude mixture was diluted withEtOH (10 mL), silica gel (3 g) was then added to this crude materialto make a solid deposit after evaporation of the EtOH. A silica gelcolumn chromatography (eluent: PE-EtOAc, 95:5) finally affordedthe pure nitrile together with the cyclic imide. Conversion into thedesired nitrile was determined by 1H NMR analysis of the crudemixture. Given yields were reported for isolated products (Table 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridine-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50.0℃; for 16.0h;Inert atmosphere; | 3-Pyridin-2-y]-[l ,2,4]thiadiazol-5-ylamine (50 mg, 0.28 mmol), 4~phenoxybenzoic acid (120 mg, 0.56 mmol), and l -[is(dimethyiamino)methylene]-lH-l,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (128 mg, 0.34 mmol) was placed in a vial. Then dissolved in DMF (3 mL, anhydrous), added N,N-diisopropylet ylamine (98 ,uL, 0.56 mmol), and stirred at 50 C for 16 h. The reaction was diluted with water and extracted with EtOAc (x 3). The combined organic layers were dried and concentrated onto celite. Purified by normal phase chromatography (solvent A CC12, solvent B CH2Cl2/MeOH. NH4OH 90: 10: 1, gradient from 0 - 50% B). Collected the desired product (25.2 mg, 0.0674 mmol, 24%). JH NMR (400 MHz, DMSO-t e) 6 ppm 7.1 1 (d, J-8.83 Hz, 2 H) 7.16 (d, J-7.66 Hz, 2 H) 7.23 - 7.31 (m, 1 H) 7.43 - 7.56 (m, 3 H) 7.98 (td, J=7.75, 1.73 Hz, i H) 8.24 (d, J-8.74 Hz, 3 H) 8.72 (d, J=4.34 Hz, 1 H) 13.71 (br. s., 1 H); LCMS (M/Z): M-H-f 375. |