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[ CAS No. 2516-95-2 ] {[proInfo.proName]}

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Product Details of [ 2516-95-2 ]

CAS No. :2516-95-2 MDL No. :MFCD00007290
Formula : C7H4ClNO4 Boiling Point : -
Linear Structure Formula :C6H3Cl(NO2)(COOH) InChI Key :ZKUYSJHXBFFGPU-UHFFFAOYSA-N
M.W : 201.56 Pubchem ID :17286
Synonyms :

Calculated chemistry of [ 2516-95-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.23
TPSA : 83.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.84
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 1.95
Log Po/w (MLOGP) : 1.11
Log Po/w (SILICOS-IT) : -0.26
Consensus Log Po/w : 1.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.461 mg/ml ; 0.00228 mol/l
Class : Soluble
Log S (Ali) : -3.51
Solubility : 0.0627 mg/ml ; 0.000311 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.77
Solubility : 3.4 mg/ml ; 0.0169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 2516-95-2 ]

Signal Word:Danger Class:9
Precautionary Statements:P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310 UN#:3077
Hazard Statements:H302-H315-H318-H335-H400 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2516-95-2 ]

* 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 [ 2516-95-2 ]
  • Downstream synthetic route of [ 2516-95-2 ]

[ 2516-95-2 ] Synthesis Path-Upstream   1~43

  • 1
  • [ 2516-95-2 ]
  • [ 16064-14-5 ]
Reference: [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801[2] Chem. Zentralbl., 1940, vol. 111, # I, p. 370
  • 2
  • [ 2516-95-2 ]
  • [ 16712-16-6 ]
  • [ 31374-18-2 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 34, p. 6517 - 6521
  • 3
  • [ 2516-95-2 ]
  • [ 635-21-2 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogen In ethanol at 20℃; To a solution of 5-chloro-2-nitrobenzoic acid (20 g, 110 mmol) in ethanol was added freshly activated raney nickel (2 g). The mixture was stirred overnight at room temperature under hydrogen atmosphere. The solution was filtered through celite and evaporated under reduced pressure to yield 16 g (96percent) of white SOLIDS. 1H NMR (DMSO-D6) : d 6.77 (d, J = 8.9 Hz, 1H), 7.24 (DD, J= 2.9, 8.9 Hz, 1H), 7.62 (d, J= 2.9 Hz, 1H), 8.7 (b, 3H); EIMS: 170 (M-H).
Reference: [1] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 1, p. 86 - 109
[2] Patent: WO2004/74218, 2004, A2, . Location in patent: Page 115-116
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2801 - 2809
[4] Chemical Biology and Drug Design, 2016, p. 710 - 723
[5] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801[6] Chem. Zentralbl., 1940, vol. 111, # I, p. 370
[7] Journal of the American Chemical Society, 1954, vol. 76, p. 6336,6337
[8] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 14, p. 5039 - 5047
[9] Chinese Chemical Letters, 2010, vol. 21, # 9, p. 1015 - 1019
[10] Asian Journal of Chemistry, 2013, vol. 25, # 2, p. 1039 - 1042
  • 4
  • [ 2516-95-2 ]
  • [ 5202-89-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2801 - 2809
[2] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
[3] Patent: WO2012/46244, 2012, A1,
[4] Patent: US2013/190490, 2013, A1,
  • 5
  • [ 2516-95-2 ]
  • [ 611-06-3 ]
YieldReaction ConditionsOperation in experiment
66% With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24 h; Schlenk technique Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,40.3 mg of 2-nitro-4-chlorobenzoic acid and 17.5 mg of sodium chloride4 mL of dimethyl sulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases were concentrated to give 25.3 mg of 2-nitro-1,5-dichlorobenzene,The yield is 66percent.
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6646 - 6648
[3] Patent: CN107325002, 2017, A, . Location in patent: Paragraph 0067
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 6
  • [ 67-56-1 ]
  • [ 2516-95-2 ]
  • [ 1882-69-5 ]
Reference: [1] Patent: CN106496036, 2017, A, . Location in patent: Paragraph 0026
  • 7
  • [ 2516-95-2 ]
  • [ 69-78-3 ]
Reference: [1] Archives of Biochemistry, 1959, vol. 82, p. 70,71
  • 8
  • [ 73033-58-6 ]
  • [ 6628-86-0 ]
  • [ 2516-95-2 ]
YieldReaction ConditionsOperation in experiment
60% With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48 h; Schlenk technique General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57percent) as a pale yellow solid. Yields of 57percent of 2a and 38percent of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 8, p. 1629 - 1639
  • 9
  • [ 2516-95-2 ]
  • [ 6628-86-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2688 - 2696
[2] Patent: WO2008/156656, 2008, A2,
  • 10
  • [ 73033-58-6 ]
  • [ 2516-95-2 ]
YieldReaction ConditionsOperation in experiment
87% With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48 h; Schlenk technique General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57percent) as a pale yellow solid. Yields of 57percent of 2a and 38percent of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 8, p. 1629 - 1639
  • 11
  • [ 73033-58-6 ]
  • [ 6628-86-0 ]
  • [ 2516-95-2 ]
YieldReaction ConditionsOperation in experiment
60% With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 48 h; Schlenk technique General procedure: To a Schlenk tube were added Fe(NO3)3·9H2O (40.6 mg, 0.1 mmol), TEMPO (15.8 mg, 0.1 mmol), KCl (7.5 mg, 0.1 mmol), 1a (108.5 mg, 1.0 mmol), and DCE (4.0 mL) sequentially under an atmosphere of oxygen (gas bag, commercial size: 2 L, which could be expanded to 5 L). The mixture was then stirred at 25 °C until completion of the reaction as monitored by TLC (petroleum ether/EtOAc = 5:1) (48h). The crude reaction mixture was filtered through a short column of silica gel (height: 2 cm, diameter: 3 cm) eluting with Et2O (3 × 25 mL). After evaporation, the residue was purified by chromatography on silica gel [petroleum ether/EtOAc = 15:1 (500 mL) to 2:1 (300 mL)] to afford benzoic acid (2a)14 (69.9 mg, 57percent) as a pale yellow solid. Yields of 57percent of 2a and 38percent of benzaldehyde (3a)15 were observed by NMR analysisof the crude product using CH2Br2 as an internal standard and by comparison with spectra reported in the literature.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 8, p. 1629 - 1639
  • 12
  • [ 535-80-8 ]
  • [ 2516-95-2 ]
Reference: [1] Patent: CN106496036, 2017, A, . Location in patent: Paragraph 0025
  • 13
  • [ 535-80-8 ]
  • [ 2516-95-2 ]
  • [ 4771-47-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 95
[2] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 215,225
[3] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 199
[4] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 95
[5] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 215,225
  • 14
  • [ 5367-28-2 ]
  • [ 2516-95-2 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 3330
[2] Asian Journal of Chemistry, 2013, vol. 25, # 2, p. 1039 - 1042
  • 15
  • [ 611-06-3 ]
  • [ 2516-95-2 ]
Reference: [1] Roczniki Chemii, 1976, vol. 50, p. 1841 - 1858
[2] Roczniki Chemii, 1976, vol. 50, p. 1841 - 1858
  • 16
  • [ 6628-86-0 ]
  • [ 2516-95-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801[2] Chem. Zentralbl., 1940, vol. 111, # I, p. 370
  • 17
  • [ 62567-91-3 ]
  • [ 2516-95-2 ]
Reference: [1] Roczniki Chemii, 1976, vol. 50, p. 1841 - 1858
  • 18
  • [ 62567-90-2 ]
  • [ 2516-95-2 ]
Reference: [1] Roczniki Chemii, 1976, vol. 50, p. 1841 - 1858
  • 19
  • [ 121-14-2 ]
  • [ 2516-95-2 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 3330
  • 20
  • [ 43192-03-6 ]
  • [ 2516-95-2 ]
Reference: [1] Chemische Berichte, 1907, vol. 40, p. 3330
  • 21
  • [ 7697-37-2 ]
  • [ 535-80-8 ]
  • [ 2516-95-2 ]
  • [ 4771-47-5 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
[2] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 95
[3] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 215,225
  • 22
  • [ 2516-95-2 ]
  • [ 31577-25-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 4, p. 824 - 827
  • 23
  • [ 2516-95-2 ]
  • [ 610-37-7 ]
YieldReaction ConditionsOperation in experiment
96.5% With sodium hydroxide In water for 72 h; Inert atmosphere 5-Chloro-2-nitrobenzoic acid (32.00 g, 0.159 mol),Dissolved in 15percent aqueous sodium hydroxide solution,The reaction was refluxed under N2 for 72h.After completion of the reaction, the pH of the solution was adjusted to 1.0, extracted with ethyl acetate, the combined ethyl acetate layers were dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure to give 28.05 g of 5-hydroxy-2-nitrobenzoic acid in a yield of 96.5percent.
90% With potassium hydroxide In water for 24 h; Reflux Step 1: (0332) Potassium hydroxide aqueous solution (13.8 g, 248 mmol, 40 ml) was added into 5-chloro-2-nitrobenzoic acid 11-a (5 g, 24.8 mmol) and the mixture was stirred at reflux for 24 hours. The pH value of the reaction mixture was adjusted to 2 with concentrated hydrochloric acid under ice-cooling, the precipitated solid was filtered and dried to give 11-b as a white solid (4.1 g, yield: 90percent).
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 43, p. 14654 - 14664
[2] Patent: CN106478548, 2017, A, . Location in patent: Paragraph 0019-0020; 0035-0036; 0051-0052; 0067-0068
[3] Patent: US2017/158680, 2017, A1, . Location in patent: Paragraph 0330; 0331; 0332
[4] Patent: WO2003/97641, 2003, A2, . Location in patent: Page/Page column 63
[5] Patent: US4348396, 1982, A,
[6] Patent: US4205173, 1980, A,
  • 24
  • [ 535-80-8 ]
  • [ 2516-95-2 ]
  • [ 4771-47-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 95
[2] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 215,225
[3] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 199
[4] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 95
[5] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 215,225
  • 25
  • [ 7697-37-2 ]
  • [ 535-80-8 ]
  • [ 2516-95-2 ]
  • [ 4771-47-5 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
[2] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 95
[3] Recueil des Travaux Chimiques des Pays-Bas, 1901, vol. 20, p. 215,225
  • 26
  • [ 2516-95-2 ]
  • [ 63860-31-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
[2] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6646 - 6648
  • 27
  • [ 2516-95-2 ]
  • [ 5922-60-1 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 18, p. 5515 - 5525
  • 28
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  • [ 21739-93-5 ]
Reference: [1] Journal of the Chemical Society, 1904, vol. 85, p. 1269
  • 29
  • [ 2516-95-2 ]
  • [ 160938-18-1 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
  • 30
  • [ 2516-95-2 ]
  • [ 74-88-4 ]
  • [ 51282-49-6 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In N,N-dimethyl-formamide at 0 - 40℃; for 1 h; Example 113; This example concerns the synthesis of Methyl ester 80: To a stirred solution of 9 (9.393 g, 46.60 mmol) in dry DMF (155 mL) at 00C was added K2CO3 <n="181"/>(13.23 g, 95.72 mmol) and MeI (19.38 g, 8.5 mL, 136.5 mmol) and warmed to 400C. After 1 h, the solution was cooled to rt and diluted with EtOAc (1 15 mL). The solution was washed with H2O (3 x 100 mL), and sat. aq. NaCl (3 x 100 mL). The dried (Na2SO4) extract was concentrated in vacuo and purified via flash chromatography over silica gel, eluting with 40-60percent EtOAc/Hexanes, to give the known methyl ester 80 (9.244 g, 42.87 mmol, 92percent) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.95 (d, J =8.7 Hz, IH), 7.73 (d, J= 2.3 Hz, IH), 7.63 (dd, J = 8.7, 2.3 Hz, IH), 3.98 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 164.7, 146.1, 139.7, 131.6, 129.8, 129.4, 125.5, 53.6.
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 26, p. 9857 - 9865
[2] Patent: WO2008/156656, 2008, A2, . Location in patent: Page/Page column 44; 179-180
  • 31
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  • [ 77-78-1 ]
  • [ 51282-49-6 ]
YieldReaction ConditionsOperation in experiment
78% With sodium carbonate In acetone for 3 h; Heating Example14:1 (Procedure R)2-(4-Chloro-phenylamino)-5-r4-(4-chlorophenylamino)phenylsulfanvnbenzoic acidStep 1 : Methyl 5-chloro-2-nitrobenzoateDimethyl sulfate (15 ml_, 150 mmol) was added dropwise to a mixture of 5-chloro-2-nitro benzoic acid (20 g, 100 mmol), Na2CO3 (15.9 g, 150 mmol) in acetone.The mixture was heated at rx for 3 h, cooled, filtered and concentrated. Extractive workup (EtOAc, water, brine), drying (Na2SO4) gave a solution from which the sub-title compound was obtained as a solid after addition of a small amount of petroleum ether and standing in the cold. Yield: 16.9 g (78percent).
534 g With potassium carbonate In [(2)H6]acetone for 0.5 h; Reflux Reference Example 1
Preparation of Methyl 5-chloro-2-nitrobenzoate
Potassium carbonate (515 gm) was added to a solution of 5-chloro-2-nitro benzoic acid (500 gm) in acetone (2750 ml) at room temperature.
Dimethyl sulphate (306.5 gm) was added to the reaction mixture slowly and heated to reflux for 30 minutes.
The reaction mass was filtered and then concentrated to obtain a residual mass.
The residual mass was poured to the ice water and extracted with methylene chloride.
The solvent was distilled off under reduced pressure to obtain a residual solid of methyl 5-chloro-2-nitrobenzoate (534 gm).
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
[2] Patent: WO2009/127822, 2009, A2, . Location in patent: Page/Page column 97
[3] Patent: WO2012/46244, 2012, A1, . Location in patent: Page/Page column 6
[4] Patent: US2013/190490, 2013, A1, . Location in patent: Paragraph 0046; 0047
  • 32
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YieldReaction ConditionsOperation in experiment
92% at 0℃; for 15 h; Heating / reflux 5-Chloro-2-nitro-benzoic acid (compound A') (5.0 g) was dissolved in methanol (150 ml). Thionyl chloride (9.5 ml) was added to the solution at 0°C, and the mixture was heated under reflux with stirring for 15 hr. After the completion of the reaction, distilled water was added thereto at 0°C, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with distilled water and saturated brine, was dried over sodium sulfate, and was then concentrated to give 5-chloro-2-nitro-benzoic acid methyl ester as a useful intermediate (12.9 g, yield 92percent).
Reference: [1] Patent: EP1614676, 2006, A1, . Location in patent: Page/Page column 161
[2] Asian Journal of Chemistry, 2011, vol. 23, # 5, p. 2007 - 2010
[3] Synthetic Communications, 2008, vol. 38, # 23, p. 4107 - 4115
[4] Patent: US2010/280268, 2010, A1, . Location in patent: Page/Page column 10
[5] Asian Journal of Chemistry, 2011, vol. 23, # 12, p. 5471 - 5476
[6] Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2573 - 2578
  • 33
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Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1900, vol. 19, p. 55
[2] Patent: US4259510, 1981, A,
  • 34
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  • [ 121-44-8 ]
  • [ 79-22-1 ]
  • [ 51282-49-6 ]
Reference: [1] Patent: US5202322, 1993, A,
[2] Patent: US5256667, 1993, A,
  • 35
  • [ 50424-28-7 ]
  • [ 2516-95-2 ]
  • [ 6705-03-9 ]
  • [ 2327-45-9 ]
Reference: [1] Patent: US5457105, 1995, A,
  • 36
  • [ 2516-95-2 ]
  • [ 2327-45-9 ]
Reference: [1] Patent: CN106478548, 2017, A,
  • 37
  • [ 2516-95-2 ]
  • [ 2475-80-1 ]
Reference: [1] Patent: CN106478548, 2017, A,
  • 38
  • [ 2516-95-2 ]
  • [ 73033-58-6 ]
  • [ 113259-79-3 ]
YieldReaction ConditionsOperation in experiment
91% With hydrogenchloride In tetrahydrofuran A solution of borane:tetrahydrofuran complex (25.8 g, 0.3 mole) in tetrahydrofuran (THF) (300 mL) was added dropwise to a stirred solution of 5-chloro-2-nitrobenzoic acid (50.0 g, 0.24 mole) in dry THF (400 mL) maintained at 0° C. under an atmosphere of nitrogen.
After completion of the addition, the mixture was heated at 50° C. for 96 hours before being cooled in an ice bath.
Hydrochloric acid (10percent solution) was added dropwise and the mixture refluxed for 30 minutes.
The THF was removed in vacuo and the residue extracted with dichloromethane (3*350 mL).
Combined extracts were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and the solvent evaporated to give a solid (45 g, 100percent), crystallization from chloroform-hexane gave 5-chloro-2-nitro-benzenemethanol (41.0 g, 91percent) mp 79°-81° C.
Anal. calcd. for C7 H6 ClNO3: C, 44.82; H, 3.22; N, 7.47. Found: C, 44.74; H, 3.19; N, 7.51.
Reference: [1] Patent: US4701459, 1987, A,
  • 39
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  • [ 73033-58-6 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 4, p. 824 - 827
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 14, p. 2688 - 2696
  • 40
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  • [ 150683-30-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
  • 41
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  • [ 160129-45-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
  • 42
  • [ 2516-95-2 ]
  • [ 137973-76-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 8, p. 1743 - 1754
  • 43
  • [ 2516-95-2 ]
  • [ 1372540-25-4 ]
Reference: [1] Patent: US2012/88767, 2012, A1,
Same Skeleton Products
Historical Records

Pharmaceutical Intermediates of
[ 2516-95-2 ]

Tolvaptan Related Intermediates

Chemical Structure| 160129-45-3

[ 160129-45-3 ]

7-Chloro-1,2,3,4-tetrahydrobenzo[b]azepin-5-one

Chemical Structure| 96515-79-6

[ 96515-79-6 ]

5-Chloro-2-fluorobenzaldehyde

Chemical Structure| 137973-76-3

[ 137973-76-3 ]

N-(4-(7-Chloro-5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carbonyl)-3-methylphenyl)-2-methylbenzamide

Chemical Structure| 51282-49-6

[ 51282-49-6 ]

Methyl 5-chloro-2-nitrobenzoate

Chemical Structure| 2969-81-5

[ 2969-81-5 ]

Ethyl 4-bromobutyrate

Related Functional Groups of
[ 2516-95-2 ]

Aryls

Chemical Structure| 6280-88-2

[ 6280-88-2 ]

4-Chloro-2-nitrobenzoic acid

Similarity: 0.99

Chemical Structure| 51282-49-6

[ 51282-49-6 ]

Methyl 5-chloro-2-nitrobenzoate

Similarity: 0.93

Chemical Structure| 4771-47-5

[ 4771-47-5 ]

3-Chloro-2-nitrobenzoic acid

Similarity: 0.93

Chemical Structure| 34662-36-7

[ 34662-36-7 ]

3-Chloro-5-nitrobenzoic acid

Similarity: 0.89

Chemical Structure| 99-60-5

[ 99-60-5 ]

2-Chloro-4-nitrobenzoic acid

Similarity: 0.87

Chlorides

Chemical Structure| 6280-88-2

[ 6280-88-2 ]

4-Chloro-2-nitrobenzoic acid

Similarity: 0.99

Chemical Structure| 51282-49-6

[ 51282-49-6 ]

Methyl 5-chloro-2-nitrobenzoate

Similarity: 0.93

Chemical Structure| 4771-47-5

[ 4771-47-5 ]

3-Chloro-2-nitrobenzoic acid

Similarity: 0.93

Chemical Structure| 34662-36-7

[ 34662-36-7 ]

3-Chloro-5-nitrobenzoic acid

Similarity: 0.89

Chemical Structure| 99-60-5

[ 99-60-5 ]

2-Chloro-4-nitrobenzoic acid

Similarity: 0.87

Carboxylic Acids

Chemical Structure| 6280-88-2

[ 6280-88-2 ]

4-Chloro-2-nitrobenzoic acid

Similarity: 0.99

Chemical Structure| 4771-47-5

[ 4771-47-5 ]

3-Chloro-2-nitrobenzoic acid

Similarity: 0.93

Chemical Structure| 34662-36-7

[ 34662-36-7 ]

3-Chloro-5-nitrobenzoic acid

Similarity: 0.89

Chemical Structure| 99-60-5

[ 99-60-5 ]

2-Chloro-4-nitrobenzoic acid

Similarity: 0.87

Chemical Structure| 96-99-1

[ 96-99-1 ]

4-Chloro-3-nitrobenzoic acid

Similarity: 0.86

Nitroes

Chemical Structure| 6280-88-2

[ 6280-88-2 ]

4-Chloro-2-nitrobenzoic acid

Similarity: 0.99

Chemical Structure| 51282-49-6

[ 51282-49-6 ]

Methyl 5-chloro-2-nitrobenzoate

Similarity: 0.93

Chemical Structure| 4771-47-5

[ 4771-47-5 ]

3-Chloro-2-nitrobenzoic acid

Similarity: 0.93

Chemical Structure| 34662-36-7

[ 34662-36-7 ]

3-Chloro-5-nitrobenzoic acid

Similarity: 0.89

Chemical Structure| 99-60-5

[ 99-60-5 ]

2-Chloro-4-nitrobenzoic acid

Similarity: 0.87