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CAS No. : | 107622-80-0 | MDL No. : | MFCD01310836 |
Formula : | C13H13NO | Boiling Point : | - |
Linear Structure Formula : | H2NCH2C6H4OC6H5 | InChI Key : | CCAZAGUSBMVSAR-UHFFFAOYSA-N |
M.W : | 199.25 | Pubchem ID : | 2760343 |
Synonyms : |
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Chemical Name : | (4-Phenoxyphenyl)methanamine |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
88% | With 5%-palladium/activated carbon; hydrogen; In methanol; for 3h;Inert atmosphere; | 4-Phenoxybenzonitrile (200 mg, 1.00 mmol) was dissolved in 8 mL MeOH and 5% Pd/C (0.2 equiv, 400 mg) was added. The reaction was stirred for 3 h under an H2 atmosphere and filtered through celite. Purification by pTLC with 10% MeOH, 2% Et3N in DCM afforded 4-phenoxybenzylamine as a white solid (179 mg,88%). 42 (1.1 equiv, 22 mg) was dissolved in toluene with 2,5-dimethoxyaniline (1 equiv, 8 mg), BINAP (0.3 equiv, 11 mg),Pd(OAc)2 (0.15 equiv, 2 mg) and Cs2CO3 (2.5 equiv, 46 mg) and the mixture was stirred for 15 h at 105 C. The solvent was removed and the crude product was filtered through silica, eluting with EtOAc. Final purification by pTLC with 50% EtOAc in hexane afforded 34 as colorless oil (12.4 mg, 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 48h; | A mixture of 1.0 g of <strong>[171178-50-0]2,6-difluoronicotinic acid</strong>, 1.4 g of WSC, 1.4 g of 4-phenoxybenzylamine and 5 ml of DMF was stirred at a room temperature for 2 days. Thereafter, a sodium bicarbonate aqueous solution was added to the reaction mixture, and it was then extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, and it was then dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.90 g of N-(4-phenoxyphenyl)methyl-<strong>[171178-50-0]2,6-difluoronicotinic acid</strong> amide. [Show Image] 1H-NMR (CDCl3) δ: 4.64 (2H, d, J = 5.4 Hz), 6.97-7.03 (6H, m), 7.09-7.14 (1H, m), 7.30-7.36 (4H, m), 8.69-8.76 (1H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With fluorosulfonyl fluoride; dihydrogen peroxide; caesium carbonate; In ethanol; water; at 20℃; for 3h; | General procedure: In this case, optimized reaction conditions are a littlebit different from those for the oxidation of anilines: 30% H2O2(6.0 equiv), Cs2CO3 (10.0 equiv), SO2F2 (balloon), EtOH/H2O = 3/1(v/v), room temperature for 3 h. |