* 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.
Reference：
[1] Journal of Organic Chemistry, 1949, vol. 14, p. 1013,1018
2
[ 52273-79-7 ]
[ 52273-77-5 ]
Reference：
[1] Collection of Czechoslovak Chemical Communications, 1995, vol. 60, # 4, p. 659 - 669
3
[ 14318-64-0 ]
[ 52273-79-7 ]
Yield
Reaction Conditions
Operation in experiment
100%
With palladium 10% on activated carbon; hydrogen In methanol for 4 h;
A solution of ethyl 2-(3-nitrophenyl)acetate (3h) (1.05 g, 3.40 mmol) inMeOH (25 mL) was hydrogenated over 10percent Pd/C (catalytic amount) for 4h. The catalyst was filtered off and the resultingsolution was concentrated to afford ethyl 2-(3-aminophenyl)acetate (4h). 1H-NMR 200 MHz (CDCl3) δ: 1.25 (t, 3H, J=7.2Hz ), 3.51 (s, 2H), 4.14 (q, 2H, J=7.2 Hz), 6.59-6.71 (m, 3H), 7.11 (t, 1 H, J=7.8 Hz). Quantitative yield.
Reference：
[1] Patent: EP3381898, 2018, A1, . Location in patent: Paragraph 0200; 0265
[2] Collection of Czechoslovak Chemical Communications, 1995, vol. 60, # 4, p. 659 - 669
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1206 - 1217
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 1, p. 217 - 220
[5] Patent: US6150373, 2000, A,
[6] Patent: US5382590, 1995, A,
[7] Patent: EP1325903, 2003, A1,
[8] Patent: WO2006/71940, 2006, A2, . Location in patent: Page/Page column 350
[9] ChemMedChem, 2018, vol. 13, # 1, p. 30 - 36
4
[ 64-17-5 ]
[ 14338-36-4 ]
[ 52273-79-7 ]
Yield
Reaction Conditions
Operation in experiment
89%
for 3 h; Heating / reflux
Example 4: Synthesis of 4- { [ (5-Phenyl-furan-2-carbonyl)- amino]-methyl}-benzoic acid (10); (a) Ethyl-3-aminophenyl acetate (6); A stirred solution of 3-aminophenyl acetic acid (1 g, 6.6 mmoles) (5) and conc. sulphuric acid (2 ml) in ethanol (20 ml) was refluxed for 3 hours. The solvent was evaporated and the residue dissolved in ethyl acetate, washed with water, sodium carbonate, brine, water, and finally dried (MgSO4). After concentrating in vacuo (6) (918mg) was obtained as dark red oil.; aa) (3-[5-(4-Fluoro-phenyl)-furan-2-carbonyl]-amino3- phenyl)-acetic acid (42); (i) Altermate sytnehsis of (3-Amino-phenyl)-acetic acid ethyl ester (6); 3-Aminophenylacetic acid (2 g, 13 mmol) was esterified with EtOH using Method B to give the title compound. Yield: 2.1 g, 89percent ; LC/MS tr 0.78 min; MS (ES+) m/z 180 (M+H)
Reference：
[1] Patent: WO2005/80367, 2005, A1, . Location in patent: Page/Page column 57; 91-92
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 2335,2338
[3] European Journal of Pharmaceutical Sciences, 2006, vol. 27, # 2-3, p. 188 - 193
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 816 - 820
5
[ 497-19-8 ]
[ 99-05-8 ]
[ 52273-79-7 ]
Yield
Reaction Conditions
Operation in experiment
82%
With sulfuric acid In ethanol
(i) 3-Aminophenylacetic Acid Ethyl Ester A solution of m-aminobenzoic acid (3.0 g; 19.8 mmol), and H2SO4 (conc.; 2 mL) in EtOH (abs.; 20 mL) was heated for 3 days at 75° C. The solution was concentrated, aqueous Na2CO3 was added, and the mixture was extracted with ether (80 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated to yield 2.9 g (82percent) of the sub-title compound. 1H-NMR (400 MHz; CDCl3): δ 7.10 (t, 1H); 6.77 (d, 1H); 6.62 (t, 1H); 6.58 (m, 1H); 4.15 (q, 2H); 3.65 (b, 2H); 3.52 (s, 2H), 1.25 (t, 3H).
Reference：
[1] Patent: US6255301, 2001, B1,
6
[ 408507-75-5 ]
[ 52273-79-7 ]
Reference：
[1] Chemische Berichte, 1954, vol. 87, p. 228,230
With palladium 10% on activated carbon; hydrogen; In methanol; for 4h;
A solution of <strong>[14318-64-0]ethyl 2-(3-nitrophenyl)acetate</strong> (3h) (1.05 g, 3.40 mmol) inMeOH (25 mL) was hydrogenated over 10% Pd/C (catalytic amount) for 4h. The catalyst was filtered off and the resultingsolution was concentrated to afford ethyl 2-(3-aminophenyl)acetate (4h). 1H-NMR 200 MHz (CDCl3) delta: 1.25 (t, 3H, J=7.2Hz ), 3.51 (s, 2H), 4.14 (q, 2H, J=7.2 Hz), 6.59-6.71 (m, 3H), 7.11 (t, 1 H, J=7.8 Hz). Quantitative yield.
9.3 g (100%)
palladium on charcoal; In ethanol;
b) A solution of 10.3 g (49 mmol) of <strong>[14318-64-0]ethyl 3-nitrophenylacetate</strong> in 120 ml of ethanol was hydrogenated over 1 g of 10% palladium on charcoal for 6 hours. The mixture was filtered and the filtrate evaporated to give 9.3 g (100%) of ethyl 3-aminophenylacetate as a yellow oil. [NMR spectrum (250 MHz) delta1.19(t) (3H), delta3.48(s) (2H), delta4.16(q) (2H), delta7.48(dd) (1H), delta7.62(d) (1H), delta8.12(m) (2H)].
In ethanol; palladium;
0.1 g of 5% palladium-on-charcoal is added to a solution of 2.0 g of <strong>[14318-64-0]ethyl 3-nitrophenylacetate</strong> in 20 cm3 of ethanol. The suspension is stirred for 2 hours at a temperature close to 25 C under a hydrogen atmosphere (100 kPa). The catalyst is then separated off by filtration and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40 C. 1.7 g of ethyl 3-aminophenylacetate are thus obtained in the form of an oil which is used as such in the subsequent syntheses. Ethyl 3-nitrophenylacetate may be prepared by the method described by Segers and A. Bruylants, Bul. Soc. Chim. Belg., 64, 87 (1955).
carbon palladium; In methanol;
Thus obtained <strong>[14318-64-0]ethyl 3-nitrophenylacetate</strong> (5.0 g, 24 mmol) was then dissolved in methanol (80 mL) together with 10 wt% of palladium/carbon (150 mg), and stirred under a hydrogen atmosphere (1 kg/cm2) for 14 hours. The reaction solution was filtered through Celite so as to remove the palladium/carbon catalyst, evaporated under reduced pressure so as to remove the solvent, and the residue was purified through silica gel column chromatography (hexane:ethyl acetate (v/v)=7:3) to thereby obtain a purified ethyl 3-aminophenylacetate (yield: 4.0 g, yield ratio: 100%) as a syrup.
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 2068.65 Torr; for 2h;
A mixture of ethyl (3-nitrophenyl)acetate (21 g, 0.1 mol) and 10% Pd/C (2 g) in MeOH (300 mL) was stirred at RT under H2 40 (psi) for 2h. The reaction mixture was filtered and the filtrate was concentrated to afford ethyl (3-aminophenyl)acetate (17 g).
(3-Methanesulfonylamino-phenyl)-acetic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridine; In tetrahydrofuran; at 20℃;
(3-Amino-phenyl)-acetic acid ethyl ester (0.895 g, 5.0 mmol) and (0.281 mL, 5.0 mmol) are added to a round bottomed flask containing THF (20 mL) and pyridine (0.60 mL). The mixture is stirred at room temperature overnight. The clear solution is diluted with EtOAc (200 mL), washed with 1N HCl (3×100 mL) and brine (100 mL), and dried with MgSO4. The solvent is evaporated in vacuo to afford intermediate 13-B as a white solid.
(3-acetylamino-phenyl)-acetic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridine; dmap; In tetrahydrofuran; at 20℃;
(3-Amino-phenyl)-acetic acid ethyl ester (0.895 g, 5.0 mmol) and acetyl chloride (0.26 mL, 5.0 mmol) are added to a round bottomed flask containing THF (20 mL), pyridine (0.60 mL) and DMAP (10 mg). The mixture is stirred at room temperature overnight. The clear solution is diluted with EtOAc (200 mL), washed with 1N HCl (3×100 mL) and brine (100 mL), and dried with MgSO4. Solvent is evaporated in vacuo to afford intermediate 14-B as a white solid that is used without further purification
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