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CAS No. : | 15118-60-2 | MDL No. : | MFCD00075052 |
Formula : | C10H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RBHLFWNKEWLHBP-UHFFFAOYSA-N |
M.W : | 179.22 | Pubchem ID : | 27049 |
Synonyms : |
|
Chemical Name : | 4-(4-Aminophenyl)butanoic acid |
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 |
---|---|---|
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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With HCl conc.; sodium carbonate; In methanol; | Step 1: Methyl-4-(4-aminophenyl)-butanoate (40) To a solution of 4-(4-aminophenyl)-butyric acid (5 g, 27.90 mmol) in MeOH (100 mL) at room temperature was added HCl conc. (37percent 15 mL). The resulting mixture was stirred overnight at 50° C. then treated with a saturated aqueous solution NaHCO3 and Na2CO3 solid until pH 9. The solvent was evaporated under reduced pressure then the aqueous phase was extracted several times with CH2Cl2. The crude material was purified by flash chromatography using CH2Cl2/MeOH as solvent mixture yielding 40 (4.93 g, 91percent) as orange solid. 1H NMR: (300 MHz, acetone-d6): 6.89 (d, J=8 Hz, 2H), 6.59 (d, J=8 Hz, 2H), 4.40 (broad s, 1H), 3.60 (s, 3H), 2.48 (t, J=7 Hz, 2H), 2.28 (t, J=7 Hz, 2H), 1.82 (qt, J=7 Hz, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sulfuric acid; sodium carbonate; In methanol; | 9A Methyl 4-(4-aminophenyl)butanoate 8.4 ml of concentrated H2SO4 was added to a solution of 4-(4-aminophenyl)butanoic acid (2.0 g, 11.6 mmo) in methanol (84 ml) and refluxed for 2 h. After that the mixture was left to cool at room temperature, added with Na2CO3 to basic pH and extracted with ethyl acetate. The organic phase was dried and the solvent was evaporated off, to obtain 1.7 g of the title compound as a colourless oil (82percent yield). 1H N.M.R. (300 MHz, CD3OD) delta ppm: 1.83 (q, 2H); 2.28 (t, 2H); 2.49 (t, 2H); 3.62 (s, 3H); 6.66 (d, 2H); 6.92 (d, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | In tetrahydrofuran; methanol; hexane; dichloromethane; at 0 - 20℃; for 1h; | To a solution of 4-(4-aminophenyl)butanoic acid (180 mg, 1 mmol) in a mixture of THF (4 ml), MeOH (1 ml) and dichloromethane (1 ml) in a 20-mL vial was added dropwise (trimethylsilyl)diazo-methane (1ml, 2N in hexane) at 0 °C. After the addition was complete, the resulting mixture was stirred at room temperature for lhr. The volatile material was removed under reduced pressure and the residue was purified by chromatography on silica gel using hexane/dichloromethane (2:1) followed by dichloromethane as eluent to give methyl 4-(4-aminophenyl)butanoate as an yellowish oil (55 mg, 28percent yield). |
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