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Chemical Structure| 35748-34-6
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CAS No. :35748-34-6 MDL No. :MFCD09842614
Formula : C8H9NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :OMWQHVRUXLRZRC-UHFFFAOYSA-N
M.W : 167.16 Pubchem ID :12782444
Synonyms :

Safety of [ 35748-34-6 ]

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:

Application In Synthesis of [ 35748-34-6 ]

* 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.

  • Upstream synthesis route of [ 35748-34-6 ]
  • Downstream synthetic route of [ 35748-34-6 ]

[ 35748-34-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 22621-41-6 ]
  • [ 35748-34-6 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In methanol at 20℃; for 49 h; Shake a suspension of methyl 2-hydroxy-3-nitrobenzoate (Step 1,18. 1 g, 93 mmol) and 5percent palladium on carbon (5 g) in methanol (200 mL) at room temperature under hydrogen (60 psi) in a Parr bottle for 49 h. Filter the mixture through a plug of Celite and remove the filtrate solvent under reduced pressure to afford methyl 3-amino-2-hydroxybenzoate (Step 2) as a yellow solid (15.6 g, >99percent) : 1H NMR (CDC13) 8 10.87 (s, 1H), 7.23 (dd, J = 7.7 Hz, 2H), 6.87 (t, J = 9.9 Hz, 1H), 3.95 (s, 3 H), 3.80 (br s, 2H) ; ESI MS m/z 168 [C8HGNO3 + H] +.
98.6% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol; ethyl acetate at 20℃; Methyl 2-hydroxy-3-nitrobenzoate (1.404 g, 7.12 mmol) in ethanol (70 ml), ethyl acetate (40 ml), was dissolved in THF (40 ml). It was stirred overnight at room temperature under a hydrogen atmosphere with 10percent palladium-carbon thereto (140 mg). After the reaction, it was filtered through Celite and evaporated to give the title compound (1.174 g, 98.6percent) as a brown solid.
95% With hydrogen In ethanol at 80℃; for 2 h; To a solution of 2-hydroxy-3-nitro-benzoic acid methyl ester (2.3 g, 11.67 mmol, 1.0 equiv) in ethanol (50 mL) was added palladium on activated charcoal 10percent (0.47 g, 0.47 mmol, 0.04 equiv), the reaction vessel filled with hydrogen (3.5 bar) and stirred at 80° C. for 2 h. The catalyst was removed by filtration over celite and the solvent removed under reduced pressure yielding 1.9 g (95percent) of the title compound which was used directly without further purification. 1H NMR (300 MHz, CDCl3): δ 3.88 (br s, 2H), 3.93 (s, 3H), 6.71 (t, J=7.9 Hz, 1H), 6.87 (dd, J=7.9 Hz, J=1.5 Hz, 1H), 7.24 (dd, J=7.9 Hz, J=1.5 Hz, 1H). 13C NMR (75 MHz, CDCl3): δ 52.13, 111.83, 118.71, 118.98, 119.55, 135.85, 149.70, 171.11.
95% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol at 20℃; for 2 h; Synthesis of (3)
To a solution of methyl 3-nitrosalicyliate (2) (108.2g, 0.549mol) in THF (1140ml)/MeOH (810ml), 10percent Pd-C (15.2g) was added, followed by catalytic-reducing with hydrogen at 1 atom and room temperature for 2 hours.
After filtering out the catalyst, it was washed with THF and then the solvent was distilled away.
The residue was washed with diisopropylether to obtain methyl 3-aminosalicyliate (3) as a brown solid of 166.7g (95percent).
94% With palladium on activated charcoal; hydrogen In tetrahydrofuran; ethyl acetate for 2.5 h; Methyl 2-hydroxy-3-nitrobenzoate (3.90 g, 19.78 mmol) was dissolved in THF/EtOAc (1:1, 100mL) in a hydrogenation bottle and there was added Pd/C (0.390 g). The reaction was shaken under H2-atmosphere (50 psi) in a Parr hydrogenation apparatus for 2 hours. The reaction mixture was filtered through a pad of Celite and the filtrate was evaporated under reduced pressure. The residue was purified by dry column vacuum chromatography (petroleum ether → EtOAc) and the collected fractions were evaporated to give the title compound (3.10 g, 94percent), as white needles. mp. 88 – 89 °C (Litt8. 88 – 89 °C). 1H NMR (300 MHz, CDCl3) δ 10.85 (d, J = 0.6 Hz, 1H), 7.21 (dd, J = 8.0, 1.6 Hz, 1H), 6.85 (ddd, J = 7.7, 1.6, 0.6 Hz, 1H), 6.69 (dd, J = 8.0, 7.7 Hz, 1H), 3.92 (s, 3H), 3.88 (br s, 3H). 13C NMR (75 MHz, CDCl3) δ 171.1, 149.7, 135.8, 119.7, 119.1, 118.8, 111.8, 52.4
88% With hydrogen In ethanol for 2 h; To a solution of 2-hydroxy-3-nitrobenzoic acid methyl ester (5 g, 25.4 mmol) in ethanol (40 mL) was added 10percent palladium on carbon (0.5 g), and the mixture was hydrogenated for 2h.
The catalyst was removed via filtration and the solvent was removed via evaporation, yielding 4.17 g (88percent) of title compound 3-amino-2-hydroxybenzoic acid methyl ester, 1l.
82.5% With palladium on activated charcoal; hydrogen In methanol for 18 h; Reflux 3.5g 3- nitro-2-hydroxybenzoate, 350 mg of palladium on carbon was dissolved in 50mL of methanol at room temperature under hydrogen gas reflux system, after for 18 h, filtered, the filtrate was dried over anhydrous sodium sulfate was added, the reaction solution was concentrated, to PE: EA = 8: 1 by column chromatography to give 2.4g white solid, yield 82.5percent.
72% With hydrogen In methanol for 7 h; Step 3: methyl 3-amino-2-hydroxybenzoate; A solution of methyl 2-hydroxy-3-nitrobenzoate (2 g, 0.010 mol) in methanol (30 ml_), was hydrogenated with a hydrogen balloon in the presence of 10percent palladium on chacoal (600 mg) for 7h. After the reaction is completed, the reaction mixture was filtered through celite bed and the filtrate was concentrated under reduced pressure to obtain 1.6 g of the above required compound (72percent) as a grey coloured solid. 1H NMR (300 MHz, CDCI3): δ (ppm) = 10.88(s, 1 H), 6.87 (d, 1 H, J=7.5Hz), 6.72 (d, 1 H, J= 7.8Hz), 3.88(s, 3H).

Reference: [1] Patent: WO2004/63155, 2004, A1, . Location in patent: Page 172
[2] Patent: JP2016/124812, 2016, A, . Location in patent: Paragraph 0138
[3] Patent: US2006/205718, 2006, A1, . Location in patent: Page/Page column 73
[4] Patent: EP2959918, 2015, A1, . Location in patent: Paragraph 0116
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
[6] Chemistry - A European Journal, 2015, vol. 21, # 52, p. 19231 - 19242
[7] Journal of Organic Chemistry, 2014, vol. 79, # 16, p. 7415 - 7424
[8] Journal of the American Chemical Society, [9] Journal of the American Chemical Society, 2009, vol. 131, p. 3342 - 3348
[10] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 4081 - 4085
[11] Patent: US2006/148823, 2006, A1, . Location in patent: Page/Page column 43-44
[12] Patent: CN104788398, 2017, B, . Location in patent: Paragraph 0046-0048
[13] Patent: WO2010/115736, 2010, A2, . Location in patent: Page/Page column 84
[14] Patent: WO2008/81399, 2008, A2, . Location in patent: Page/Page column 72
[15] Archiv der Pharmazie, 2008, vol. 341, # 6, p. 386 - 392
[16] Patent: WO2009/16560, 2009, A2, . Location in patent: Page/Page column 40; 70
[17] Patent: US2010/16401, 2010, A1, . Location in patent: Page/Page column 35
[18] Patent: WO2010/19606, 2010, A1, . Location in patent: Page/Page column 77
[19] Patent: WO2007/51062, 2007, A2, . Location in patent: Page/Page column 138
[20] Patent: US2006/35882, 2006, A1, . Location in patent: Page/Page column 31
[21] Patent: WO2013/37960, 2013, A1, . Location in patent: Page/Page column 85
  • 2
  • [ 91983-31-2 ]
  • [ 35748-34-6 ]
YieldReaction ConditionsOperation in experiment
59% With sodium acetate In water; ethyl acetate at 25℃; for 16 h; Example 114 Cmethyl 3-amino-2-hydroxybenzoate; A suspension of methyl 5-bromo-2-hydroxy-3-nitrobenzoate (38.4 g, 0.14 mol), sodium acetate (19.63 g, 0.24 mol) and 10percent Pd/C (3.84 g) in ethyl acetate (500 mL) and water (30 mL) was stirred at 25° C. under 1 atm of hydrogen for 16 hr. The mixture was filtered and the filtrate was washed with water (500 mL.x.2), brine (300 mL), dried over anhydrous sodium sulfate and concentrated to give crude product. The crude product was washed with methanol at 0° C. to give methyl 3-amino-2-hydroxybenzoate (13.67 g, yield 59percent) as a light yellow solid. 1H-NMR (400 MHz, CDCl3-d) δ 3.88-3.94 (s, br, 2H), 3.91 (s, 3H), 6.70-6.74 (t, J=7.8 Hz, 1H), 6.88-6.90 (m, 1H), 7.24-7.26 (m, 1H), 10.91 (s, 1H); LC-MS (ESI) m/z 168 [M+1]-.
Reference: [1] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 56
  • 3
  • [ 67-56-1 ]
  • [ 570-23-0 ]
  • [ 35748-34-6 ]
YieldReaction ConditionsOperation in experiment
45% at 0 - 70℃; for 12 h; Inert atmosphere Synthesis of methyl 3-amino-2-hydroxybenzoate (XVII):XVIITo a stirred solution of 3-amino-2-hydroxybenzoic acid XII (0.5 g, 3.26 mmol) in MeOH (15 ml) was added sulfuric acid (1 ml) at 0°C under nitrogen atmosphere and the resulting mixture was heated at 70°C for 12 h. After completion of reaction, the reaction mixture was cooled, concentrated, washed with saturated NaHCC>3 solution and extracted with ethyl acetate. The organic layer was dried over Na2S04 and evaporated under reduced pressure to afford product XVII in 45percent yield.
25.9% for 55 h; Heating / reflux (1)
methyl 3-aminosalicylate
3-Aminosalicylic acid (690 mg, 4.51 mmol), methanol (45 ML), and conc. sulfuric acid (0.9 ML) were mixed, and heated for 55 hours under reflux..
The methanol was distilled off under reduced pressure..
To the residue was added cooled water..
The aqueous residue was made alkaline by addition of aqueous saturated sodium hydrogen carbonate under cooling with ice..
Thus precipitated crystalline product were collected by filtration, washed with two portions of water, and dried in vacuo at 40°C for 40 min., to give 710 mg of a pale pink crystalline product..
The product was suspended in chloroform (35 ML), and insolubles were removed by filtration..
The filtrate was dried over sodium sulfate and then concentrated under reduced pressure to give 181 mg (yield 25.9percent) of the desired compound in the form of a brown crystalline product. 1H NMR (CDCl3, 400 MHz) δ: 3.88 (2H, broad s), 3, 94 (3H, s), 6.71 (1H, dd, J=8Hz, 8Hz), 6.87 (1H, d, J=8Hz), 7.24 (1H, m), 10.88 (1H, s).
19% at 20℃; for 22 h; Heating / reflux EXAMPLE 392
3-[(2-Chlorobenzoyl)Amino]-2-[(2-Chlorophenyl)Methoxy]Benzoic Acid
A mixture of thionyl chloride (1.15 ML, 15.8 mmol) and methanol (20.0 ML) was stirred at room temperature for 30 min then treated with 3-amino-2-hydroxybenzoic acid (1.5 g, 9.79 mmol).The reaction mixture was stirred at room temperature for 2 h, refluxed for 20 h, cooled and concentrated.The crude product was partitioned between EtOAc (100 ML) and 5percent NAHCO3 solution (65 ML), back-extracting the aqueous phase with EtOAc (4*100 ML).The organic phase was washed with water (2*20 ML) and brine (20 ML), dried (MgSO4), filtered and concentrated to give a dark red solid (381 mg, 19percent).
Reference: [1] Patent: WO2011/72174, 2011, A1, . Location in patent: Page/Page column 146-147
[2] Patent: EP1452528, 2004, A1, . Location in patent: Page 18
[3] Patent: US2003/225091, 2003, A1, . Location in patent: Page 71
  • 4
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  • [ 42753-75-3 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567
  • 5
  • [ 85-38-1 ]
  • [ 35748-34-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
[2] Patent: EP2959918, 2015, A1,
  • 6
  • [ 119-36-8 ]
  • [ 35748-34-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 4081 - 4085
[2] Patent: CN104788398, 2017, B,
  • 7
  • [ 69-72-7 ]
  • [ 35748-34-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 16, p. 4081 - 4085
[2] Patent: CN104788398, 2017, B,
  • 8
  • [ 119-36-8 ]
  • [ 35748-34-6 ]
  • [ 42753-75-3 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567
  • 9
  • [ 35748-34-6 ]
  • [ 122-51-0 ]
  • [ 1086378-35-9 ]
YieldReaction ConditionsOperation in experiment
91% With ytterbium(III) triflate In toluene at 100℃; for 1 h; Microwave irradiation Methyl 3-amino-2-hydroxybenzoate (1.69 g, 10.13 mmol) was suspended in toluene (2 mL) in a microwave vial. HC(OEt)3 (1.80 g, 12.15 mmol) and Yb(OTf)3 (0.003 g, 0.005 mmol) was added and the reaction was heated at 100 °C for 1 hour in the microwave. The reaction mixture was evaporated and purified by flash chromatography (petroleum ether/EtOAc 4:1) to give the title compound (1.63 g, 91percent) as pale yellow crystals. mp. 116 – 118 °C (Litt9. 77 °C). 1H NMR (300 MHz, CDCl3) δ 8.21 (s, 1H), 8.04 (dd, J = 7.8, 1.2 Hz, 1H), 7.99 (dd, J = 8.0, 1.2 Hz, 1H), 7.44 (dd, J = 8.0, 7.8 Hz), 3.76 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 180.9, 164.4, 153.4, 141.4, 128.0, 125.6, 124.5, 115.4, 52.6
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
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