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[ CAS No. 52913-11-8 ]

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Chemical Structure| 52913-11-8
Chemical Structure| 52913-11-8
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CAS No. :52913-11-8 MDL No. :MFCD07366754
Formula : C9H11NO2 Boiling Point : 281.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :165.19 g/mol Pubchem ID :13054266
Synonyms :

Safety of [ 52913-11-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 52913-11-8 ]

  • Upstream synthesis route of [ 52913-11-8 ]
  • Downstream synthetic route of [ 52913-11-8 ]

[ 52913-11-8 ] Synthesis Path-Upstream   1~9

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Reference: [1] Journal of the American Chemical Society, 1917, vol. 39, p. 2437
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YieldReaction ConditionsOperation in experiment
91% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 16 h; (3-Amino-phenyl)-acetic acid methyl ester: To a solution of (3-Nitro-phenyl)-acetic acid methyl ester (0.50 g; 2.55 mmol) in methanol (30.0 ml.) was added palladium on carbon (10percent w/w) (0.20 g; 0.19 mmol) portion wise under nitrogen atmosphere. The reaction mixture was hydrogenated under hydrogen atmosphere (bladder pressure) at RT for 16 h. The reaction mixture was filtered through celite, washed with methanol (75 mL) and the filtrate was concentrated to afford (3- Amino-phenyl)-acetic acid methyl ester 0.40 g (91 percent) as a brown solid. HPLC MS (Agilent - Waters Xbridge C8 (50x4.6 mm, 3.5 pm); 2.0 mlJmin; 220nm; buffer A: 0.1percent TFA/H20, buffer B: 0.1percent TFA/ACN; (0.0-8.0min 5percent-100percent buffer B; 8.0-8.1 min 100percent buffer B; 8.1-8.5min 100percent-5percent buffer B; 8.5-10.Omin 5percent-5percent buffer B): (M+H) 166.0; Rt. 1.39 min.
Reference: [1] Patent: WO2016/50359, 2016, A1, . Location in patent: Page/Page column 97
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1206 - 1217
[3] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 10, p. 1601 - 1608
[4] Patent: WO2011/60196, 2011, A1, . Location in patent: Page/Page column 142
[5] Patent: WO2013/131408, 2013, A1, . Location in patent: Page/Page column 71
[6] Patent: WO2014/99633, 2014, A2, . Location in patent: Page/Page column 96
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  • [ 67-56-1 ]
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YieldReaction ConditionsOperation in experiment
87% for 2 h; Heating / reflux (3-Amino-phenyl)-acetic acid methyl ester (3a). Thionyl chloride (4.8 mL, 66.16 mmol) was carefully added drop wise to MeOH (100 mL) at 0 0C. To the resulting solution was added a suspension of 3-amino-phenylacetic acid (5.0 g, 33.08 mmol) in MeOH (100 mL) and the reaction mixture was refluxed for 2 h. Then MeOH was distilled off and the residue was partitioned between EtOAc and sat. aq. NaHCO3. The phases were separated and the organic phase was washed with sat. aq. NaHCO3, dried (Na2SO4) and evaporated which gave the title compound (4.77, 87percent).
87%
Stage #1: at 0℃; for 2 h; Heating / reflux
Stage #2: With water; sodium hydrogencarbonate In ethyl acetate
(3-Amino-phenyl)-acetic acid methyl ester (40a); Thionyl chloride (4.8 mL, 66.16 mmol) was carefully added drop wise to MeOH (100 mL) at 0 0C. To the resulting solution was added a suspension of 3-amino-phenylacetic acid (5.0 g, 33.08 mmol) in MeOH (100 mL) and the reaction mixture was refluxed for 2 h. Then MeOH was distilled off and the residue was partitioned between EtOAc and sat. aq. NaHCO3. The phases were separated and the organic phase was washed with sat. aq. NaHCO3, dried (Na2SO4) and evaporated to give 4.77 (87percent) of the title compound.
83% at 0℃; for 4 h; 3-AMINOPHENYLACETIC acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0 °C. Thionyl chloride (11.2 ML, 0.15 mol) was added dropwise under stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2SO4). Methyl 3-aminophenylacetate was isolated as a brown oil. (14. 1g, 83percent). 1H NMR (500 MHz, CDC13) 8 7.12 (1H, dd), 6.7-6. 6 (3H, m), 3.71 (3H, s), 3.55 (2H, s). Methyl (3-Methanesulfonylamino-phenyl)-acetate : Methyl 3-aminophenylacetate
83%
Stage #1: at 0℃; for 4 h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
Methyl 3-aminophenylacetate:; 3-Aminophenylacetic acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0 °C. Thionyl chloride (11.2 mL, 0.15 mol) was added dropwise under stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2S04). Methyl 3-aminophenylacetate was isolated as a brown oil. (14.1g, 83percent). 1H NMR (500 MHz, CDC13) 8 7.12 (1H, dd), 6.7 - 6.6 (3H, m), 3.71 (3H, s), 3.55 (2H, s).
83% at 0℃; for 4 h; Methyl 3-aminophenylacetate: 3-Aminophenylacetic acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0 °C. Thionyl chloride (11.2 mL, 0.15 mol) was added dropwise under stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 ML) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2SO4). Methyl 3-aminophenylacetate was isolated as a brown oil. (14. 1g, 83percent).APOS;H NMR (500 MHz, CDCL3) 8 7.12 (1H, dd), 6.7- 6.6 (3H, m), 3.71 (3H, s), 3.55 (2H, s).
83% at 0℃; for 4 h; Example 15; 3-(Methanesulfonylamino)phenylacetic acid:; Step A: 3-Aminophenylacetic acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0 °C. Thionyl chloride (11.2 mL, 0.15 mol) was added dropwise while stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2SO4) to afford methyl 3-aminophenylacetate as a brown oil. (14.1g, 83percent). 1H NMR (CDCl3) No. 7.12 (1H, dd), 6.7 - 6.6 (3H, m), 3.71 (3H, s), 3.55 (2H, s).
77% for 18 h; Heating / reflux Example 6; a) (3-f [5-(2-Methoxy-phenyl)-furan-2-carbonyl]-amino}- phenyl)-acetic acid (17); (i) (3-Amino-phenyl)-acetic acid methyl ester (15); 3-Aminophenylacetic acid (5 g, 33.1 mmol) was esterified with MeOH using Method B to give the title compound Yield: 4.22 g, 77percent; LC/MS tr 0.70 min; MS (ES+) m/z 166 (M+H); A solution of carboxylic acid (1 eq) was heated under reflux for 18 h with H2SO4 (0.5 vol) in MeOH or EtOH (25 vol). The solvent was evaporated in vacuo and the residue partitioned between DCM and aqueous sodium bicarbonate. The DCM layer was washed with brine, dried (Na2SO4), filtered and the solvent removed in vacuo to give the ester.

Reference: [1] Patent: WO2009/53277, 2009, A1, . Location in patent: Page/Page column 52
[2] Patent: WO2008/107365, 2008, A1, . Location in patent: Page/Page column 83
[3] Patent: WO2005/19190, 2005, A2, . Location in patent: Page/Page column 56
[4] Patent: WO2005/103050, 2005, A2, . Location in patent: Page/Page column 171
[5] Patent: WO2004/41813, 2004, A1, . Location in patent: Page 117
[6] Patent: WO2005/105780, 2005, A2, . Location in patent: Page/Page column 70
[7] Patent: WO2005/80367, 2005, A1, . Location in patent: Page/Page column 64; 70
[8] Journal of the American Chemical Society, 1917, vol. 39, p. 2437
[9] Patent: WO2011/38572, 2011, A1, . Location in patent: Page/Page column 61
[10] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3502 - 3522
[11] Patent: EP1486491, 2004, A1, . Location in patent: Page 60
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YieldReaction ConditionsOperation in experiment
92% With sulfuric acid In methanol for 48 h; Heating / reflux Step 1: Dissolve (3-Amino-phenyl)-acetic acid ((24),700mg, 4.63mmol) in MeOH (21mL) and add conc. sulfuric acid (0.27mL, 5.09mmol). Stir the reaction mixture for 2d under reflux. Cooled mixture to room temperature (rt), remove solvent under reduced pressure and prepurify the residue by flushing it over a short pad of silica gel using EtOAc. Remove solvent again and partitione the residue between EtOAc and saturated aqu. NaHCO3 (1+1). Extracte the aqueous layer 3 times with EtOAc, washe the combined organic layers with brine and dried with Na2SO4. Remove solvent under reduced pressure and dry the residue without further purification in oil pump vacuum to obtain product (25) as a light yellow oil (708mg, 92percent). 1H NMR (400MHz, CDCl3): 3.51 (s, 2 H); 3.67 (s, 3 H); 6.57 (dd, 1 H, J1 = 7.8Hz, J2 = 1.BHz); 6.60 (br.Ψt, 1 H, J = 1.8Hz); 6.65 (br.d, 1 H, J 7.8Hz); 7.08 (Ψt, 1 H, J = 7.8Hz).
92% With sulfuric acid In methanol at 20℃; for 48 h; Heating / reflux Dissolve (3-Amino-phenyl)-acetic acid ((22),700mg, 4.63mmol) in MeOH (2 1 mL) and add conc. sulfuric acid (0.27mL, 5.09mmol). Stir the reaction mixture for 2d under reflux. Cooled mixture to room temperature (rt), remove solvent under reduced pressure and prepurify the residue by flushing it over a short pad of silica gel using EtOAc. Remove solvent again and partition the residue between EtOAc and saturated aqu. NaHCO3 (1+1). Extracte the aqueous layer 3 times with EtOAc, washe the combined organic layers with brine and dried with Na2SO4. Remove solvent under reduced pressure and dry the residue without further purification in oil pump vacuum to obtain product (23) as a light yellow oil (708mg, 92percent). 1H NMR (400MHz, CDCl3): 3.51 (s, 2 H); 3.67 (s, 3 H); 6.57 (dd, 1 H, J1 = 7.8Hz, J2 = 1.8Hz); 6.60 (br.Ψt, 1 H, J= 1.8Hz); 6.65 (br.d, 1 H, J 7.8Hz); 7.08 (Ψt, 1 H, J= 7.8Hz).
79% With HCl conc.; sodium hydrogencarbonate In methanol; hexane; ethyl acetate Methyl-3-aminophenylacetate (1)
To a solution of 3-aminophenylacetic acid (3 g, 19.85 mmol) in methanol (50 mL) at room temperature was added HCl conc. (37percent, 7.5 mL).
The mixture was stirred 6 h at room temperature then treated with a saturated aqueous solution of NaHCO3.
The solvent was removed under reduced pressure then the aqueous phase was extracted several times with CH2Cl2.
The combined organic extracts were dried over (MgSO4) and evaporated.
The crude mixture was purified by flash chromatography using hexane/AcOEt (1:1) yielding 1 as a yellow oil (3.06 g, 79percent).
1H NMR: (300 MHz, CDCl3): 7.10 (t, J=8 Hz, 1H), 6.68-6.58 (m, 3H), 3.69-3.65 (m, 5H), 3.53 (s, 2H).
Reference: [1] Patent: EP1577289, 2005, A1, . Location in patent: Page/Page column 18
[2] Patent: EP1764093, 2007, A1, . Location in patent: Page/Page column 18-19
[3] Patent: EP775133, 2001, B1,
[4] Patent: US6541661, 2003, B1,
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Reference: [1] Patent: US5610144, 1997, A,
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  • [ 1877-73-2 ]
  • [ 52913-11-8 ]
Reference: [1] Patent: WO2014/99633, 2014, A2,
[2] Patent: WO2016/50359, 2016, A1,
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  • [ 52913-11-8 ]
Reference: [1] Patent: WO2011/60196, 2011, A1,
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Reference: [1] Patent: WO2011/60196, 2011, A1,
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  • [ 1455473-56-9 ]
  • [ 52913-11-8 ]
Reference: [1] Patent: WO2013/131408, 2013, A1,
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