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CAS No. : | 20637-09-6 | MDL No. : | MFCD07366753 |
Formula : | C11H15NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CLKHQWJXESOLCJ-UHFFFAOYSA-N |
M.W : | 193.24 | Pubchem ID : | 88628 |
Synonyms : |
|
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: |
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* 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 hydrogen;palladium on activated charcoal; In methanol; for 3h; | b) Methyl 4-(4-aminophenyl)butanoateA suspension of methyl 4-(4-nitrophenyl)butanoate (3.05 g, 13.67 mmol) and Pd/C (1.0 g, 10percent Pd on activated C, 1.09 mmol) in MeOH (40 ml_) was stirred under H2 atmosphere (balloon) for 3 h. The reaction mixture was filtered through Celite (washing with EtOAc). Solvent was concentrated off, to furnish 2.33 g of methyl 4-(4-aminophenyl)butanoate (brown solid, yield: 88percent). It was submitted to next step without purification.1H NMR (CDCI3, 250 MHz) delta ppm: 6.96 (d, J = 8.5 Hz, 2H), 6.63 (d, J = 8.2 Hz, 2H), 3.66 (s, 3H), 2.55 (t, J = 7.6 Hz, 2H), 2.31 (t, J = 7.7 Hz, 2H), 1.90 (q, J = 7.6 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The material so obtained was dissolved in a mixture of methanol (200 ml) and water (100 ml) and heated to reflux on a steam bath. Ferrous sulphate heptahydrate (11.71 g) and iron powder (34.0 g) were added and the mixture was heated to reflux for 6 hours. The solution was filtered whilst hot. Methanol was evaporated from the filtrate and the residual aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried and evaporated to give a residue which was purified by column chromatography on silica gel using methylene chloride as eluent. There was thus obtained methyl 4-(4-aminophenyl)butyrate (6.22 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sulfuric acid; for 1.5h;Reflux; | A 250-mL round bottom flask was charged with 4-(4-aminophenyl)butyric acid (2.00 g, 11.2 mmol) in methanol (50 mL) and treated with cone, sulfuric acid (1 mL). The resultant mixture was heated to reflux for 1.5 h. After this time, methanol (-25 mL) was distilled off. The reaction was cooled to 60 °C and methyl tert-butyl ether was added. The mixture was allowed to slowly cool to room temperature, then diluted with hexanes (50 mL) to afford a white solid. The solid was dissolved in THF (6 mL)/water (4 mL) and treated with cone. NH4OH (6 mL). The mixture was diluted with dichloromethane (50 mL) and the layers separated. The organic layer was washed with saturated sodium chloride (5 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (2.07 g, 96percent) as a brown solid. MW = 193.24. ]H NMR (DMSO-i, 500 MHz) delta 6.83-6.79 (m, 2H), 6.50-6.46 (m, 2H), 4.81 (s, 2H), 3.57 (s, 3H), 2.39 (t, J = 7.5 Hz, 2H), 2.25 (t, 7 = 7.5 Hz, 2H), 1.73 (quin, / = 7.5 Hz, 2H). |
70% | With thionyl chloride; In methanol; at 0 - 80℃; for 16h; | Synthesis of cyanoamine 28Preparation of methyl 4-(4-aminophenyl)butanoate 27.[00200] To a mixture of compound 26 (0.92 g, 5.13 mmol) in CH30H (20 mL) was added dropwise thionyl chloride (1.9 mL , 25.7 mmol) at OoC with stirring. After addition, the reaction mixture was stirred at 80 oC for 16 h, concentrated in vacuo. The residue was diluted with aqNaHC03, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04 and concentrated to dryness to give compound 27 (0.7 g, 70percent) as a light yellow solid. 1H NMR (400 MHz, CDC13) 56.97 (d, 2H, J=8.3 Hz), 6.64 (d, 2H, J=8.3 Hz), 3.68 (br s, 2H), 3.66(s, 3H), 2.54 (t, 2H, J=7.4 Hz), 2.3 l(t, 2H, J=7.4 Hz), 1.85- 1.95(m, 2H). |
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