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Product Details of [ 635-21-2 ]

CAS No. :635-21-2 MDL No. :MFCD00007838
Formula : C7H6ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IFXKXCLVKQVVDI-UHFFFAOYSA-N
M.W : 171.58 Pubchem ID :12476
Synonyms :

Calculated chemistry of [ 635-21-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.82
TPSA : 63.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 1.57
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 0.48
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 1.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.23
Solubility : 1.01 mg/ml ; 0.00588 mol/l
Class : Soluble
Log S (Ali) : -2.51
Solubility : 0.53 mg/ml ; 0.00309 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.02
Solubility : 1.63 mg/ml ; 0.00948 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.09

Safety of [ 635-21-2 ]

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 [ 635-21-2 ]

* 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 [ 635-21-2 ]
  • Downstream synthetic route of [ 635-21-2 ]

[ 635-21-2 ] Synthesis Path-Upstream   1~60

  • 1
  • [ 32315-10-9 ]
  • [ 635-21-2 ]
  • [ 4743-17-3 ]
YieldReaction ConditionsOperation in experiment
97% at 80℃; Step 1
6-Chloro-1H-benzo[d]1,3-oxazine-2,4-dione
A 500 mL 3-necked round bottom flask was charged with 2-amino-5-chlorobenzoic acid (17 g, 0.1 mol) and 1,2-dichloroethane (200 mL).
To the above was added dropwise a solution of triphosgene (21 g, 0.21 mol) in 1,2-dichloroethane (100 mL) at 80° C.
The resulting mixture was heated at 80° C. for further 3 h then cooled in ice-water.
The precipitate was collected by filtration and dried to afford 19 g (97percent) of the product as white solid. 1H NMR (300 MHz, DMSO-d6) δ: 11.85 (br, 1H), 7.88 (d, J=2.4 Hz, 1H), 7.78 (dd, J=8.7, 2.4 Hz, 1H), 7.15 (d, J=8.7 Hz, 1H).
97% at 80℃; for 3 h; A 500 mL 3-necked round bottom flask was charged with 2-amino-5- chlorobenzoic acid (17 g, 0.1 mol) and 1 ,2-dichloroethane (200 mL). To the above was added dropwise a solution of triphosgene (21 g, 0.21 mol) in 1,2- dichloroethane (100 mL) at 80 °C. The resulting mixture was heated at 80 °C for further 3 h then cooled in ice- water. The precipitate was collected by filtration and dried to afford 19 g (97percent) of the product as white solid. *H NMR (300 MHz, DMSO-d6) δ: 11.85 (br, 1H), 7.88 (d, J = 2.4 Hz, 1H), 7.78 (dd, J = 8.7, 2.4 Hz, 1H), 7.15 (d, J = 8.7 Hz, 1H).
Reference: [1] Patent: US2010/120741, 2010, A1, . Location in patent: Page/Page column 78
[2] Patent: WO2011/112731, 2011, A2, . Location in patent: Page/Page column 174
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6434 - 6456
[4] Chemical Biology and Drug Design, 2010, vol. 75, # 5, p. 444 - 454
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2295 - 2299
[6] Tetrahedron Letters, 2014, vol. 55, # 26, p. 3607 - 3609
[7] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
[8] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 2006 - 2017
[9] Chemical Biology and Drug Design, 2018, vol. 92, # 5, p. 1914 - 1919
  • 2
  • [ 635-21-2 ]
  • [ 503-38-8 ]
  • [ 4743-17-3 ]
YieldReaction ConditionsOperation in experiment
92% at 20℃; for 4 h; Heating / reflux Trichloromethyl CHLOROFORMATE (4.8 mL, 300 mmol) was added to a stirred solution of Compound 57 (6.84 g, 40 mmol) in dry dioxane at room temperature and the solution was refluxed for 4 h. The solution was cooled in an ice bath and the solids formed were filtered. The solids were washed by ether and dried under vacuum at room temperature to yield 7.3 g (92percent) of white SOLIDS. H NMR (DMSO-D6) : d 7.47 (d, J= 8.6 Hz, 1H), 7.70 (dd, J= 8.6, 1.8 Hz, 1H), 7.82 (d, J= 1.1, 1H), 11.63 (S, 1H).
Reference: [1] Patent: WO2004/74218, 2004, A2, . Location in patent: Page 116
  • 3
  • [ 201230-82-2 ]
  • [ 635-21-2 ]
  • [ 4743-17-3 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 4196 - 4200
  • 4
  • [ 79-37-8 ]
  • [ 635-21-2 ]
  • [ 4743-17-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 1, p. 138 - 147
  • 5
  • [ 75-44-5 ]
  • [ 635-21-2 ]
  • [ 4743-17-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 1983, vol. 18, # 3, p. 241 - 247
  • 6
  • [ 77287-34-4 ]
  • [ 635-21-2 ]
  • [ 16064-14-5 ]
YieldReaction ConditionsOperation in experiment
93.3% at 150℃; for 2 h; Examples 13 to 21:; The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the type of the anthranilic acid derivative was changed. The results are shown in Table 4.
90% at 140℃; General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 °C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2*2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 .x. 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 .x. 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.
Reference: [1] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 8
[2] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[3] Chemistry and Biodiversity, 2017, vol. 14, # 4,
[4] Molecules, 2006, vol. 11, # 6, p. 383 - 392
[5] Journal of Medicinal Chemistry, 1983, vol. 26, # 3, p. 420 - 425
[6] Journal of the American Chemical Society, 1946, vol. 68, p. 1303
[7] Journal of the Indian Chemical Society, 1959, vol. 36, p. 787,789, 790
[8] Huaxue Xuebao, 1956, vol. 22, p. 335,336[9] Scientia Sinica (English Edition), 1958, vol. 7, p. 1035,1036
[10] Journal of Organic Chemistry, 1952, vol. 17, p. 149,153
[11] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801[12] Chem. Zentralbl., 1940, vol. 111, # I, p. 370
[13] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 8, p. 1203 - 1207
[14] Biochemistry, 2017, vol. 56, # 49, p. 6491 - 6502
[15] Chemistry and Biodiversity, 2018, vol. 15, # 6,
  • 7
  • [ 6313-33-3 ]
  • [ 635-21-2 ]
  • [ 16064-14-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 19, p. 3860 - 3873
  • 8
  • [ 635-21-2 ]
  • [ 16064-14-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
  • 9
  • [ 635-21-2 ]
  • [ 7253-22-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
[2] Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 8, p. 1203 - 1207
[3] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 7, p. 907 - 911
[4] Journal of the American Chemical Society, 1946, vol. 68, p. 1303
[5] Journal of the Indian Chemical Society, 1959, vol. 36, p. 787,789, 790
[6] Oriental Journal of Chemistry, 2010, vol. 26, # 4, p. 1401 - 1406
[7] Patent: WO2016/91774, 2016, A1,
  • 10
  • [ 77287-34-4 ]
  • [ 635-21-2 ]
  • [ 7253-22-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 4, p. 417 - 420
  • 11
  • [ 635-21-2 ]
  • [ 2034-23-3 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 4, p. 735 - 742
[2] Heterocycles, 2004, vol. 62, p. 869 - 876
  • 12
  • [ 108-24-7 ]
  • [ 635-21-2 ]
  • [ 7142-09-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 119 - 132
  • 13
  • [ 635-21-2 ]
  • [ 75-05-8 ]
  • [ 7142-09-8 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 31, p. 4362 - 4365
  • 14
  • [ 635-21-2 ]
  • [ 7142-09-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1721 - 1728
[2] European Journal of Medicinal Chemistry, 2014, vol. 86, p. 613 - 627
[3] Patent: WO2015/19121, 2015, A1,
  • 15
  • [ 57-13-6 ]
  • [ 635-21-2 ]
  • [ 20028-68-6 ]
YieldReaction ConditionsOperation in experiment
49.5% for 1 h; Reflux 5-Chloro-2-aminobenzoic acid (0.429 g, 2.5 mmol), urea (0.33 g, 5.5 mmol), phosphorus pentachloride (3.124 g, 15 mmol) and phosphorus oxychloride (10 mL) were added and the reaction was stopped by heating to reflux for 1 h. Decompression to steam Excess phosphorus oxychloride, the residue was dissolved in methylene chloride, ice water was washed with phosphorus oxychloride and phosphorus pentachloride, the separation of water The organic phase was adjusted to pH 6-7 with saturated sodium bicarbonate and extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate. Concentration column chromatography gave 0.289 g of a light yellow solid, yield: 49.5percent
Reference: [1] Patent: CN102250075, 2016, B, . Location in patent: Paragraph 0697; 0698
[2] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2755 - 2766
  • 16
  • [ 635-21-2 ]
  • [ 20028-68-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
[2] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 75 - 80
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7717 - 7727
[4] RSC Advances, 2017, vol. 7, # 36, p. 22360 - 22368
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 1, p. 265 - 285
[6] Molecules, 2018, vol. 23, # 2,
[7] Patent: CN107652273, 2018, A,
  • 17
  • [ 57-13-6 ]
  • [ 635-21-2 ]
  • [ 1640-60-4 ]
YieldReaction ConditionsOperation in experiment
94% at 200℃; for 3 h; Step 1
6-Chloroquinazoline-2,4(1H,3H)-dione
A 250 mL round bottom flask was charged with 2-amino-5-chlorobenzoic acid (17.2 g, 0.1 mol) and urea (30 g, 0.5 mol).
The resulting mixture was heated to 200° C. for 3 h.
Work up:
the reaction mixture was washed by water and filtered.
The solid was dried to give 18.5 g (94percent) of the product. MS m/z: 196 (M+H+).
94% at 200℃; for 3 h; A 250 mL round bottom flask was charged with 2-amino-5- chlorobenzoic acid (17.2 g, 0.1 mol) and urea (30 g, 0.5 mol). The resulting mixture was heated to 200 °C for 3 h. Work up: the reaction mixture was washed by water and filtered. The solid was dried to give 18.5 g (94percent) of the product. MS m/z: 196 (M+H+)
79% at 150℃; for 10 h; General procedure: A mixture of 2-aminobenzoic acid 3a (2.00 g, 14.91 mmol), urea (4.40 g,73.26 mmol) in phenol (6.00 g, 63.76 mmol) was heated at 150 Cunder the reflux for 10 h. The reaction mixture was cooled downto 100 C and ethanol/water (1:1) 10 mL was added drop-wise.The reaction mixture was cooled to rt, filtered, washed with ethanol(5 mL), and dried to afford 4a in 53percent yield (1.26 g).
Reference: [1] Patent: US2010/120741, 2010, A1, . Location in patent: Page/Page column 24
[2] Patent: WO2011/112731, 2011, A2, . Location in patent: Page/Page column 79
[3] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7717 - 7727
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 6, p. 2390 - 2400
[6] Tetrahedron, 2012, vol. 68, # 43, p. 8908 - 8915
[7] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5141 - 5156
[8] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 75 - 80
  • 18
  • [ 917-61-3 ]
  • [ 635-21-2 ]
  • [ 1640-60-4 ]
YieldReaction ConditionsOperation in experiment
44%
Stage #1: With acetic acid In water at 30℃; for 0.5 h;
Stage #2: With sodium hydroxide In water at 30℃;
Stage #3: With hydrogenchloride In water
Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-ammo-5-chlorobenzoic acid (10 g, 58 48 mmol, 1 00 equiv) in water (100 mL), acetic acid (8 g, 133 33 mmol, 2 24 equiv) This was followed by the addition of NaOCN (8 2 g, 126 15 mmol, 2 13 equiv) The mixture was stirred for 30 rains at 3O0C To this was added sodium hydroxide (86 g, 2 15 mol, 37 00 equiv) The resulting solution was stirred overnight at 30cC The solids were collected by filtration The residue was dissolved in water The pH value of the solution was adjusted to 7 with hydrogen chloπde (12 mol/L) The solids were collected by filtration This resulted in 5 g (44percent) of 6 chloroqmnazolme-2,4(lH,3H)-dione as a white solid.
Reference: [1] Patent: WO2010/78449, 2010, A2, . Location in patent: Page/Page column 235
  • 19
  • [ 590-28-3 ]
  • [ 635-21-2 ]
  • [ 1640-60-4 ]
Reference: [1] Chemistry Letters, 2005, vol. 34, # 10, p. 1438 - 1439
[2] Chinese Chemical Letters, 2012, vol. 23, # 4, p. 431 - 433
[3] Journal of Chemical Research, 2007, # 6, p. 358 - 361
  • 20
  • [ 635-21-2 ]
  • [ 1640-60-4 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 25, p. 8457 - 8478
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 940
[3] Patent: US5688803, 1997, A,
  • 21
  • [ 635-21-2 ]
  • [ 101861-61-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1953, vol. 583, p. 150,155
[2] Patent: WO2011/112731, 2011, A2,
  • 22
  • [ 56-81-5 ]
  • [ 635-21-2 ]
  • [ 6456-78-6 ]
YieldReaction ConditionsOperation in experiment
68.91%
Stage #1: at 65 - 140℃; for 5.5 - 7.5 h;
Stage #2: at 0℃;
Example-2; 6-Chloro-l ,2,3,4-tetrahydro-quinoline-8-carboxylic acid (4-/er/-butyl-benzyl)-[2-(4- fluoro-phenyl)-ethyl]-amide, hydrochloride salt a) Concentrated sulfuric acid (73.83 g, 0.80 mol) was added dropwise to a vigorously stirred mixture of 2-amino-5-chloro-benzoic acid (90 g, 0.524 mol), I2 (1.65g, 6.4 mmol) in glycerol within 30 minutes, wherein the temperature of the mixture rises to 65-70 0C. The mixture was then heated to 135-140 0C for 5-7 hrs giving a dark brown foaming mixture. The reaction mixture was cooled to room temperature and poured into 1500 ml of ice water. The pH of the mixture was adjusted to 6.5 by adding 25-30 percent ammonia solution. The precipitated compound was filtered, washed with cold water and dried over P2O5 to get brown solid. of 6-chloro- quinoline-8-carboxylic acid (75 g) (Yield=68.91 percent).
68.91%
Stage #1: at 20 - 140℃;
Stage #2: With ammonia In water; glycerol
Concentrated sulfuric acid (73.83 g, 0.80 mol) was added dropwise to a vigorously stirred mixture of 2-amino-5-chloro-benzoic acid (90 g, 0.524 mol), I2 (1.65 g, 6.4 mmol) in glycerol within 30 minutes, wherein the temperature of the mixture rises to 65-70° C. The mixture was then heated to 135-140° C. for 5-7 hrs giving a dark brown foaming mixture. The reaction mixture was cooled to room temperature and poured into 1500 ml of ice water. The pH of the mixture was adjusted to 6.5 by adding 25-30percent ammonia solution. The precipitated compound was filtered, washed with cold water and dried over P2O5 to get brown solid of 6-chloro-quinoline-8-carboxylic acid (75 g) (Yield=68.91percent).
7.9% at 65 - 140℃; for 6.5 h; 1.01 g of 5-chloroanthranilic acid and 26.6 mg of iodine were mixed with 0.7 6 g of glycerol, and the mixture was vigorously stirred,0.44 ml of concentrated sulfuric acid was added dropwise at 65 ° C. to 70 ° C. over a period of 30 minutes and the reaction was carried out at 140 ° C. for 6 hours. Then,17 mL of water at 0 ° C. was added and the pH6.5 was filtered, the solid was washed with cold water and then dried. The obtained residue was dissolved in chloroform,Insolubles were removed by filtration, activated carbon was added to adsorb impurities, and the activated carbon was removed by filtration.The solvent was distilled off, and the residue obtained was recrystallized in a mixed solution of chloroform and ethyl acetate, and the obtained crystals were washed with ethyl acetate.The solvent was distilled off to obtain 96.2 mg (yield 7.9percent) of the compoundWas obtained. For this compound, NMR, mass spectrum,The melting point was measured, and the compound 2 having the structure of the general formula 3(6-chloroquinoline-8-carboxylic acid) was confirmed.
Reference: [1] Patent: WO2008/59513, 2008, A2, . Location in patent: Page/Page column 14
[2] Patent: US2009/171091, 2009, A1, . Location in patent: Page/Page column 6
[3] Patent: JP2018/52866, 2018, A, . Location in patent: Paragraph 0046
  • 23
  • [ 635-21-2 ]
  • [ 719-59-5 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 74, p. 10503 - 10506
  • 24
  • [ 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).
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[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
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[10] Asian Journal of Chemistry, 2013, vol. 25, # 2, p. 1039 - 1042
  • 25
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  • [ 635-21-2 ]
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  • 26
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  • [ 635-21-2 ]
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  • 28
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  • [ 635-21-2 ]
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  • [ 635-21-2 ]
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  • 36
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[3] Nippon Kagaku Zasshi, 1959, vol. 80, p. 1038,1039[4] Chem.Abstr., 1961, p. 5510
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Reference: [1] Zhurnal Obshchei Khimii, 1953, vol. 23, p. 606,609; engl. Ausg. S. 629, 632
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Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 143, p. 910[2] Bulletin de la Societe Chimique de France, 1907, vol. <4> 1, p. 224
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Reference: [1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 842,844[2] Chem. Zentralbl., 1939, vol. 110, # I, p. 1366
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Reference: [1] Zhurnal Obshchei Khimii, 1937, vol. 7, p. 842,844[2] Chem. Zentralbl., 1939, vol. 110, # I, p. 1366
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Reference: [1] Zhurnal Obshchei Khimii, 1953, vol. 23, p. 606,609; engl. Ausg. S. 629, 632
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Reference: [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801[2] Chem. Zentralbl., 1940, vol. 111, # I, p. 370
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Reference: [1] Chemical Science, 2015, vol. 6, # 6, p. 3454 - 3460
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  • 49
  • [ 67-56-1 ]
  • [ 635-21-2 ]
  • [ 5202-89-1 ]
YieldReaction ConditionsOperation in experiment
100% at 0℃; for 12 h; Reflux Example 1006-Chloro-3 ,3 -dimethyl-2- (3 -morpholin-4-yl-phenyl)- 1 ,2,3 ,4-tetrahydro-quinoline-8- carboxylic acidTo a stirred solution of 2-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropwise at 0 °C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-amino-5-chloro- benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8C1N02 (M+H)+: 186.61, observed: 185.9.
100% at 0℃; for 12 h; Reflux To a stirred solution of 2-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropwise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-amino-5-chloro-benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8ClNO2 (M+H)+: 186.61, observed: 185.9.
Reference: [1] Patent: WO2011/128251, 2011, A1, . Location in patent: Page/Page column 187
[2] Patent: US2011/257151, 2011, A1, . Location in patent: Page/Page column 69
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2801 - 2809
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 143, p. 910[5] Bulletin de la Societe Chimique de France, 1907, vol. <4> 1, p. 224
[6] Journal of Medicinal Chemistry, 1996, vol. 39, # 17, p. 3248 - 3255
[7] Scientia Pharmaceutica, 2003, vol. 71, # 4, p. 331 - 356
[8] Tetrahedron Letters, 2006, vol. 47, # 26, p. 4365 - 4368
[9] Chemistry of Heterocyclic Compounds, 2006, vol. 42, # 1, p. 64 - 69
[10] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 2, p. 415 - 420
[11] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8332 - 8338
[12] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 11175 - 11183
[13] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 1919 - 1925
  • 50
  • [ 635-21-2 ]
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YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In water; acetone (109-8)
5-Chloroanthranilic acid (15.0 g), (CH3)2SO4 (11.6 g) and K2CO3 (12.7 g) were refluxed in acetone (150 g) for 30 minutes.
The mixture was concentrated to about 90 g, and thereto was added water (90 g).
The mixture was extracted with toluene (75 g), and the organic layer was concentrated to give methyl 5-chloroanthranilate (15.6 g, 96percent).
1H NMR (CDCl3, 400 MHz) δ 7.83 (d, 1H, J=2.6 Hz), 7.21 (dd, 1H, J=8.5 and 2.6 Hz), 6.61 (d, 1H, J=8.5 Hz), 5.73 (brs, 2H), 3.88 (s, 3H).
96% With potassium carbonate In water; acetone (109-8)
5-Chloroanthranilic acid (15.0 g), (CH3)2SO4 (11.6 g) and K2CO3 (12.7 g) were refluxed in acetone (150 g) for 30 minutes.
The mixture was concentrated to about 90 g, and thereto was added water (90 g).
The mixture was extracted with toluene (75 g), and the organic layer was concentrated to give methyl 5-chloroanthranilate (15.6 g, 96 percent).
1H NMR (CDCl3, 400MHz) δ 7.83 (d, 1H, J=2.6Hz), 7.21 (dd, 1H, J=8.5 and 2.6Hz), 6.61 (d, 1H, J=8.5Hz), 5.73 (brs, 2H), 3.88 (s, 3H).
Reference: [1] Patent: US2003/181496, 2003, A1,
[2] Patent: EP1479384, 2004, A1,
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Reference: [1] Patent: US5599814, 1997, A,
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3386 - 3396
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Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 45, p. 8029 - 8033
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Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 10, p. 3315 - 3318
[2] Chemical Communications, 2018, vol. 54, # 74, p. 10503 - 10506
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Reference: [1] Chemical Science, 2015, vol. 6, # 6, p. 3454 - 3460
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Reference: [1] Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 6, p. 1852 - 1872
[2] Chemical Communications, 2013, vol. 49, # 31, p. 3254 - 3256
[3] Organic Letters, 2015, vol. 17, # 17, p. 4180 - 4183
[4] Journal of Organic Chemistry, 2017, vol. 82, # 4, p. 2263 - 2268
[5] Organic Letters, 2017, vol. 19, # 7, p. 1578 - 1581
[6] Organic Letters, 2018, vol. 20, # 2, p. 345 - 348
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Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
  • 58
  • [ 635-21-2 ]
  • [ 37585-25-4 ]
YieldReaction ConditionsOperation in experiment
93% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5 h; General procedure: To a suspension of lithium aluminum hydride (20.4 mmol) in THF (10 mL) was added benzoic acid (8.5 mmol) dissolved in THF (24 mL) dropwise over 20 minutes at room temperature. The reaction continued to stir at room temperature for 3.5 h, and then was quenched at 0 °C with H2O (10 mL). The suspension was filtered through a Celite plug with EtOAc (100 mL), washed with brine (30 mL), dried with MgSO4 and concentrated in vacuo.
88%
Stage #1: With lithium aluminium tetrahydride In diethyl ether at 20℃; Cooling with ice
Stage #2: With water; sodium hydroxide In diethyl ether
Preparation of (2-amino-phenyl)-methanols (2) by reduction of 2-amino- benzoic acids (3) - General procedure; [0078] 2-Amino-benzoic acid (14 mmol) in dry diethyl ether (15 ml_) is added dropwise to an ice cooled solution of lithium aluminum hydride (15 mmol) in dry diethyl ether (100 mL) and stirred at room temperature for 2 h. Water (8 ml) is added dropwise, followed by 1M aqueous sodium hydroxide solution (13 mL). The organic layer is collected, dried over sodium sulfate and concentrated under reduced pressure. The crude product is used in the next step without further purification.; (2-Amino-5-chloro-phenyl)-methanol; Yield 88percent; 1H NMR (DMSO): 4.31 (d, 5 Hz, 2H); 5.01 (br s, 2H); 5.11 (t, 5 Hz, 1 H); 6.58 (d, 9 Hz, 1 H); 6.94 (dd, 9 and 2 Hz, 1 H) and 7.07 (d, 2 Hz, 1 H). [0080](2-Amino-3,5-dichloro-phenyl)-methanolYield 98percent; ^1H NMR (DMSO): 4.38 (d, 5 Hz1 2H); 5.22 (br s, 2H); 5.33 (t, 5 Hz, 1 H); 7.12 and 7.23 (both d, 3 Hz, both 1 H).
Reference: [1] ACS Catalysis, 2013, vol. 3, # 4, p. 622 - 624
[2] Organic Letters, 2017, vol. 19, # 12, p. 3219 - 3222
[3] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3795 - 3799
[4] Patent: WO2010/37533, 2010, A1, . Location in patent: Page/Page column 44
[5] Organic Letters, 2016, vol. 18, # 21, p. 5572 - 5575
[6] Tetrahedron Letters, 1995, vol. 36, # 41, p. 7527 - 7530
[7] Patent: US4164407, 1979, A,
[8] Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4252 - 4255
[9] Tetrahedron Letters, 2011, vol. 52, # 45, p. 5913 - 5917
[10] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[11] Tetrahedron, 2014, vol. 70, # 34, p. 5114 - 5121
[12] Tetrahedron, 2014, vol. 70, # 34, p. 5114 - 5121
[13] Synthesis (Germany), 2014, vol. 46, # 24, p. 3365 - 3373
[14] Organic Letters, 2015, vol. 17, # 19, p. 4750 - 4753
[15] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
[16] Tetrahedron Letters, 2017, vol. 58, # 45, p. 4264 - 4268
[17] Organic Letters, 2018, vol. 20, # 6, p. 1526 - 1529
[18] Organic and Biomolecular Chemistry, 2018, vol. 16, # 12, p. 2039 - 2042
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Reference: [1] Organic Letters, 2012, vol. 14, # 6, p. 1444 - 1447
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