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[ CAS No. 93-50-5 ] {[proInfo.proName]}

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Chemical Structure| 93-50-5
Chemical Structure| 93-50-5
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Product Details of [ 93-50-5 ]

CAS No. :93-50-5 MDL No. :MFCD06801386
Formula : C7H8ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :WOXLPNAOCCIZGP-UHFFFAOYSA-N
M.W : 157.60 Pubchem ID :7143
Synonyms :

Calculated chemistry of [ 93-50-5 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.35
TPSA : 35.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 1.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.677 mg/ml ; 0.0043 mol/l
Class : Soluble
Log S (Ali) : -2.22
Solubility : 0.946 mg/ml ; 0.006 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.77
Solubility : 0.268 mg/ml ; 0.0017 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 93-50-5 ]

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 [ 93-50-5 ]

* 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 [ 93-50-5 ]
  • Downstream synthetic route of [ 93-50-5 ]

[ 93-50-5 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 6627-53-8 ]
  • [ 93-50-5 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With iron; ammonium chloride In water for 0.25 h; Heating / reflux
Stage #2: Heating / reflux
A suspension of ferrum (5.0 equiv.), ammonium chloride (0.65 equiv.), and distilled water were refluxed for fifteen minutes. The nitro compound (1.0 equiv.) was added and the resulting reaction mixture was allowed to stir at reflux. When TLC showed that the reaction had stopped the mixture was neutralized by drop wise addition of a 5percent aqueous solution of sodium bicarbonate and it was filtered through Celite. The filtrate was washed thrice with ethyl acetate. The combined organic layers were washed once with brine and once with a 5percent aqueous solution of hydrochloric acid. The combined water layers were neutralized with 20percent aqueous sodium hydroxide and extracted thrice with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and the solvent removed in vacuo. The pure product was obtained using column chromatography in ethyl acetate and hexanes but sometimes the product was kept crude. The purity of the product was determined using 1H- NMR.; 4-Chloro-2-methoxy-phenylamine was obtained from Ferrum (2.23 g, 40 mmol) ammonium chloride (278 mg, 5.2 mmol), water (48 mL) and 5-chloro-2-nitroanisole (1.5 g, 8.0 mmol) as a crude mixture, which was a dark purple oil (1.15g, 91 percent). The reaction was complete in 1.5 hours. 1H NMR (300 MHz, CDCl3): δ(ppm) 6.78(m, 2H), 6.65(d, IH), 3.86(s, 3H). EPO <DP n="81"/>4-Chloro-2-methoxy-phenylamine was obtained from Ferrum (4.47 g, 80.0 mmol) ammonium chloride (556 mg, 10.4 mmol), water (80 mL) and 5-chloro-2-nitroanisole (3.0 g, 16.0 mmol) as a crude mixture, which was a dark purple oil (2.35g, 93percent). The reaction was complete in 2 hours. No 1H-NMR was performed.
76% With 5%-palladium/activated carbon; hydrogen In methanol for 72 h; A. A suspension of 5-chloro-2-nitroanisole (7s) (2.67 g, 14.2 mmol) and 5percent Pt/C (200 nig) in methanol (60 niL) was placed under a hydrogen gas atmosphere and stirred 3 days. The suspension was filtered through diatoniaceous earth and concentrated. Purification by column chromatography (40 g), eluting with 15 to 30percent EA/hexanes, gave compound 7b (1.69 g, 76percent). 1H NMR (CHLOROFORM-d) δ: 6.70 - 6.83 (m, 2H), 6.58 - 6.64 (m, 1H), 3.84 (s, 3H), 3.76 (br. s., 2H). ESI-MS (m/z): Calcd. for C7H8ClNO: 158.0 (M+1); found: 158.0.
69.5% With hydrogen In tetrahydrofuran at 20℃; 5-Chlor-2-nitroanisol in THF are hydrogenated in the presence of H2 and Raney nickel at room temperature overnight. The catalyst is separated by filtration and the filtrate evaporated to dryness. The residue is purified by chromatography (35 g silica gel, eluent : DICHLOROMETHANE : methanol = 99 : 1). Yield : 69.5 percent, brown oil
65%
Stage #1: With water; tin(ll) chloride In ethanol for 18 h; Heating / reflux
Stage #2: With sodium hydroxide In ethanol; water at 20℃;
A mixture of 4-chloro-2-methoxy-l -nitrobenzene (938 mg, 5.0 mmol), tin(II) chloride dihydrate (3.38 g, 15 mmol) and EtOH (25 mL) was heated at reflux for 18 h. After cooling to rt, NaOH (aq, 4M, 50 mL) was added. The mixture was extracted with Et2O (3x20 mL) and the combined extracts dried (Na2SO4) and concentrated. Purification by chromatography gave the title compound (511 mg, 65percent) as a red oil which solidified on standing.1H NMR (DMSO-J6, 400 MHz) δ 6.78 (IH, d), 6.67 (IH, dd), 6.57 (IH, d), 4.82 (2H, S)3 3.75 (3H, s).
64%
Stage #1: With sodium dithionite; potassium hydrogencarbonate In methanol; water at 20℃; for 2 h;
Stage #2: With hydrogenchloride In methanol; water at 60℃; for 2 h;
Preparation 91; 4-Chloro-2-methoxy-phenvlamine; To a suspension of 5-chloro-2-nitroanisole (10g, 53mmol) and potassium bicarbonate (28g, 280mol) in methanol (150mL) and water (150mL) was added sodium dithionite (28g, 159 mmol). The mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was acidified to pH1 with concentrated hydrochloric acid and the resulting brown suspension was heated for 2 hours at 60°C before the solvent was evaporated under reduced pressure. The residual aqueous solution was washed with ethyl acetate, basified with sodium hydroxide pellets and re-extracted with ethyl acetate. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the title compound in 64percent yield (5.35g). 'H NMR (DMSO-D6, 400MHz) zu : 3.66 (s, 3H), 4.76 (bs, 2H), 6.52 (m, 1H), 6.65 (m, 1 H), 6.79 (m, 1 H)
64% With sodium dithionite; potassium hydrogencarbonate In methanol; water at 20℃; for 2 h; Preparation 37; (4-Chloro-2-methoxyphenyl)amine; Sodium dithionite (28g, 159mmol) was added portionwise to a mixture of 5-chloro-2-nitroanisole (1Og, 53mmol) and potassium hydrogen carbonate (28g, 275.6mmol) in methanol (15OmL) and water (15OmL) and the reaction mixture was stirred at room temperature for 2 hours. The mixture was then acidified with concentrated hydrochloric acid and the mixture was heated at 6O0C for 2 hours. The reaction mixture was then concentrated in vacuo and the aqueous residue was washed with ethyl acetate. The aqueous solution was then basified with sodium hydroxide and extracted with ethyl acetate. The organic solution was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound in 64percent yield, 5.35g. 1HNMR(400MHz, DMSO-Cl6) δ: 3.74(s, 3H), 4.78(s, 2H), 6.58(m, 1 H), 6.65(m, 1 H), 6.77(s, 1 H)

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 3864 - 3867
[2] ChemMedChem, 2014, vol. 9, # 5, p. 962 - 972
[3] Patent: WO2006/71730, 2006, A1, . Location in patent: Page/Page column 79; 80
[4] Patent: WO2014/28805, 2014, A1, . Location in patent: Page/Page column 65
[5] Patent: WO2004/37789, 2004, A2, . Location in patent: Page 312
[6] Patent: WO2007/51982, 2007, A1, . Location in patent: Page/Page column 39
[7] Patent: WO2005/82866, 2005, A2, . Location in patent: Page/Page column 92
[8] Patent: WO2006/100588, 2006, A1, . Location in patent: Page/Page column 54
[9] Journal of the Chemical Society, 1926, p. 543[10] Journal of the Chemical Society, 1928, p. 628
[11] Collection of Czechoslovak Chemical Communications, 1978, vol. 43, # 7, p. 1747 - 1759
[12] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 5, p. 619 - 622
[13] Patent: US2005/20645, 2005, A1,
[14] Patent: CN104163764, 2016, B, . Location in patent: Paragraph 0050-0053
  • 2
  • [ 90-04-0 ]
  • [ 93-50-5 ]
YieldReaction ConditionsOperation in experiment
76% With copper(II) choride dihydrate; lithium chloride hydrate In ethanol for 7 h; Reflux General procedure: A round-bottomed flask (25 mL) was charged with substrate (2 mmol), CuCl2·2H2O (6 mmol), LiCl·H2O (2 mmol) and EtOH (4 mL). The resulting reaction mixture was stirred at reflux. After the completion of the reaction monitored by TLC, EtOH was removed under reduced pressure. Then ammonium hydroxide (4 mL, 25percent) and water (10 mL) were added and the aqueous phase was extracted with ethyl acetate (10 mL×3). The combined organic phase was washed with brine (8 mL×3) and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The crude mixture was purified by chromatography on silica gel to obtain the desired products.
Reference: [1] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 744 - 748
[2] Synthetic Communications, 2018, vol. 48, # 20, p. 2708 - 2714
  • 3
  • [ 135055-92-4 ]
  • [ 93-50-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 572 - 578
  • 4
  • [ 854910-68-2 ]
  • [ 93-50-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 459
[2] Patent: US1792156, 1929, ,
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 459
[4] Patent: US1792156, 1929, ,
  • 5
  • [ 57479-70-6 ]
  • [ 93-50-5 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 572 - 578
  • 6
  • [ 90-04-0 ]
  • [ 93-50-5 ]
  • [ 95-03-4 ]
Reference: [1] Patent: US2069546, 1935, ,
[2] Patent: US2069546, 1935, ,
  • 7
  • [ 1226-63-7 ]
  • [ 93-50-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 459
[2] Patent: US1792156, 1929, ,
  • 8
  • [ 91-23-6 ]
  • [ 93-50-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1903, vol. &lt;2&gt; 67, p. 152,153,163[2] Journal fuer Praktische Chemie (Leipzig), 1903, vol. &lt;2&gt; 68, p. 208
  • 9
  • [ 91-23-6 ]
  • [ 93-50-5 ]
  • [ 90-04-0 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 1685
[2] Chemische Berichte, 1899, vol. 32, p. 2623[3] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1899, p. 1625
  • 10
  • [ 88-73-3 ]
  • [ 93-50-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1903, vol. &lt;2&gt; 67, p. 152,153,163[2] Journal fuer Praktische Chemie (Leipzig), 1903, vol. &lt;2&gt; 68, p. 208
  • 11
  • [ 611-07-4 ]
  • [ 93-50-5 ]
Reference: [1] Journal of the Chemical Society, 1926, p. 543[2] Journal of the Chemical Society, 1928, p. 628
  • 12
  • [ 97-52-9 ]
  • [ 93-50-5 ]
Reference: [1] Journal of the Chemical Society, 1959, p. 1808,1809
  • 13
  • [ 854910-68-2 ]
  • [ 93-50-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 459
[2] Patent: US1792156, 1929, ,
  • 14
  • [ 56-23-5 ]
  • [ 24251-12-5 ]
  • [ 5877-56-5 ]
  • [ 93-50-5 ]
Reference: [1] Gazzetta Chimica Italiana, 1936, vol. 66, p. 639,645
  • 15
  • [ 93-50-5 ]
  • [ 755027-21-5 ]
Reference: [1] Journal of the American Chemical Society, 1935, vol. 57, p. 1592,1594
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 3981 - 3984
  • 16
  • [ 93-50-5 ]
  • [ 1567373-49-2 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With hydrogenchloride; acetic acid; sodium nitrite In water at 0 - 60℃; for 1.5 h;
Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0℃; for 0.5 h;
General procedure: B. To a suspension of compound 7b (1 .69 g, 10.7 mmol, 1 eq) in concentrated HCl (25 mL) and acetic acid (10 mL) at 0 °C was added a solution of sodium nitrite (740 mg, 10.7 mmol, 1 eq) in water (10 mL) dropwise. The suspension was warmed to 60 °C for 1.5 hrs. The solution was cooled to 0 °C and a solution of SnCl2 (5.32 g, 23.6 mmol, 2.2 eq) in concentrated HCl (25 mL) was added. After 30 minutes, a precipatate was collected by filtration to give compound 7c (2.06 g, 93percent). 1H NMR (DMSO-d6) δ: 9.94 (br. s., 2H), 7.72 (br. s., 1H), 7.07 (s, 1H), 7.00 (s, 2H). 3.85 (s, 3H). Following the procedure described above for Example 7 and substituting the appropriate reagents, starting materials and purification methods known to those skilled in the art, the following intermediates to compounds of the present invention were prepared:
Reference: [1] Patent: WO2014/28805, 2014, A1, . Location in patent: Page/Page column 65; 66
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