* 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.
With trifluorormethanesulfonic acid In dichloromethane at 80℃; for 1 h; High pressure; Inert atmosphere; Green chemistry
General procedure: Trifluoromethane sulfonic acid (3 eq.) was gently added to a cooled (0 °C) solution of a 3-Phenylpropionic acid (0.5 mmol) in dry CH2Cl2 (1.0 mL) in a 12 mL Q-tube™ pressure tube, furnished by QLabtech. The temperature was raised to room temperature. A Teflon septum was placed on the top of the tube and the appropriate cap and pressure adapter were used. The mixture was heated in an oil bath at 80 °C. The reaction was monitored by TLC and GC/MS until the reactant disappeared. The mixture was poured into ice and extracted three times with CH2Cl2. The organic phase collected was dried on Na2SO4, filtered and concentrated under vacuum. The desired pure product was separated from the crude by flash chromatography.
66%
Stage #1: With oxalyl dichloride In dichloromethane for 8 h; Stage #2: With aluminum (III) chloride In dichloromethane for 6 h; Reflux
To a stirred solution of 4-chlorocinnamic acid (1.0g, 5.46mmol) in EtOAc (20mL) was added Pd on carbon (0.12g, 0.11mmol) at room temperature under H2atmosphere. The mixture was stirred for 10h. The resulting mixture was filtered through celite and the solvent of the filtrate was removed in vacuo. The concentrated product was employed without further purification in the next reaction. Oxalyl chloride (0.96mL, 10.92mmol) was cautiously added to a solution of the 3-(4-chlorophenyl)propanoic acid in CH2Cl2(20mL). The mixture was stirred for 8h and then the solvent was removed vacuo. The appropriate acid chloride was employed without further workup in the next reaction step. To a stirred solution of acid chloride in CH2Cl2(20mL) was added portionwise AlCl3(0.82g, 6.22mmol) at room temperature and heated under reflux for 6h. The resulting mixture was poured into ice-water and the aq. phase was extracted with CH2Cl2,washed with 1N aq. NaOH and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to produce the title compound (0.59 g, 66 percent).1H NMR (400 MHz, CDCl3) δ 2.64-2.78 (m, 2H), 3.04-3.17 (m, 2H), 7.41 (d,J=7.9, 1H), 7.55 (dd,J=8.2, 1H), 7.65-7.75 (m, 1H).
Reference：
[1] Molecules, 2014, vol. 19, # 5, p. 5599 - 5610
[2] Patent: WO2017/150904, 2017, A1, . Location in patent: Paragraph 402-404
[3] Synthetic Communications, 2007, vol. 37, # 13, p. 2171 - 2177
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 8, p. 2554 - 2558
[5] Polish Journal of Chemistry, 1991, vol. 65, # 11, p. 2057 - 2060
[6] European Journal of Medicinal Chemistry, 1976, vol. 11, # 1, p. 83 - 88
[7] Chemische Berichte, 1969, vol. 102, p. 3656 - 3665
[8] Journal of Medicinal Chemistry, 1972, vol. 15, p. 341 - 344
[9] Archiv der Pharmazie, 1975, vol. 308, # 2, p. 94 - 109
[10] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 407 - 412
[11] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1333 - 1336
[12] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 399 - 408
[13] Letters in Drug Design and Discovery, 2014, vol. 11, # 5, p. 578 - 585
[14] Patent: WO2005/123724, 2005, A1,
[15] Letters in Drug Design and Discovery, 2018, vol. 16, # 2, p. 111 - 118
4
[ 201230-82-2 ]
[ 78704-49-1 ]
[ 14548-38-0 ]
Reference：
[1] Journal of Organic Chemistry, 1993, vol. 58, # 20, p. 5386 - 5392
5
[ 52085-96-8 ]
[ 14548-38-0 ]
Yield
Reaction Conditions
Operation in experiment
84%
at 20 - 45℃; for 4.5 h;
In a 250-mL four-necked flask equipped with a tail suction, 120 g of anhydrous hexafluoroisopropanol and 1 g of anhydrous ferric chloride were added; at 20° C., 20 g of p-chlorophenylpropionyl chloride was slowly added dropwise; The reaction was incubated at 25°C for 3 hours, and the temperature was raised to 45°C for 1.5 hours until the acyl chloride was completely converted and no hydrogen chloride tail gas was released. After cooling to room temperature, the solvent was degassed under negative pressure and reconstituted with 15 ml of methanol.Crystallization gave 13.7 g of 6-chloro-1-indanone in a yield of 84percent.
Reference：
[1] Patent: CN107673956, 2018, A, . Location in patent: Paragraph 0023; 0024
[2] Chemische Berichte, 1942, vol. 75, p. 1730,1735
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1333 - 1336
[4] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 399 - 408
[5] Patent: WO2005/77907, 2005, A1, . Location in patent: Page/Page column 19; 36-37
[6] Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 449 - 469
[7] ChemMedChem, 2010, vol. 5, # 4, p. 552 - 558
[8] Patent: WO2005/123724, 2005, A1, . Location in patent: Page/Page column 48; 92
6
[ 69975-65-1 ]
[ 14548-38-0 ]
Reference：
[1] Bioorganic and medicinal chemistry, 2003, vol. 11, # 2, p. 251 - 263
[2] Chemistry - A European Journal, 2015, vol. 21, # 37, p. 13052 - 13057
7
[ 1313762-44-5 ]
[ 14548-38-0 ]
Reference：
[1] Chemical Communications, 2011, vol. 47, # 23, p. 6635 - 6637
8
[ 104-88-1 ]
[ 14548-38-0 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1333 - 1336
[2] Letters in Drug Design and Discovery, 2014, vol. 11, # 5, p. 578 - 585
[3] Letters in Drug Design and Discovery, 2018, vol. 16, # 2, p. 111 - 118
Reference：
[1] Chemische Berichte, 1892, vol. 25, p. 2115
21
[ 14548-38-0 ]
[ 3970-51-2 ]
Reference：
[1] Journal of Chemical Research, 2010, # 6, p. 325 - 329
[2] Bulletin de la Societe Chimique de France, 1973, p. 3096 - 3099
[3] Patent: WO2009/23754, 2009, A1,
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8812 - 8829
22
[ 14548-38-0 ]
[ 89-20-3 ]
Reference：
[1] Chemische Berichte, 1892, vol. 25, p. 2115
With trifluorormethanesulfonic acid; In dichloromethane; at 80℃; for 1h;High pressure; Inert atmosphere; Green chemistry;
General procedure: Trifluoromethane sulfonic acid (3 eq.) was gently added to a cooled (0 C) solution of a 3-Phenylpropionic acid (0.5 mmol) in dry CH2Cl2 (1.0 mL) in a 12 mL Q-tube pressure tube, furnished by QLabtech. The temperature was raised to room temperature. A Teflon septum was placed on the top of the tube and the appropriate cap and pressure adapter were used. The mixture was heated in an oil bath at 80 C. The reaction was monitored by TLC and GC/MS until the reactant disappeared. The mixture was poured into ice and extracted three times with CH2Cl2. The organic phase collected was dried on Na2SO4, filtered and concentrated under vacuum. The desired pure product was separated from the crude by flash chromatography.
66%
To a stirred solution of 4-chlorocinnamic acid (1.0g, 5.46mmol) in EtOAc (20mL) was added Pd on carbon (0.12g, 0.11mmol) at room temperature under H2atmosphere. The mixture was stirred for 10h. The resulting mixture was filtered through celite and the solvent of the filtrate was removed in vacuo. The concentrated product was employed without further purification in the next reaction. Oxalyl chloride (0.96mL, 10.92mmol) was cautiously added to a solution of the 3-(4-chlorophenyl)propanoic acid in CH2Cl2(20mL). The mixture was stirred for 8h and then the solvent was removed vacuo. The appropriate acid chloride was employed without further workup in the next reaction step. To a stirred solution of acid chloride in CH2Cl2(20mL) was added portionwise AlCl3(0.82g, 6.22mmol) at room temperature and heated under reflux for 6h. The resulting mixture was poured into ice-water and the aq. phase was extracted with CH2Cl2,washed with 1N aq. NaOH and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to produce the title compound (0.59 g, 66 %).1H NMR (400 MHz, CDCl3) delta 2.64-2.78 (m, 2H), 3.04-3.17 (m, 2H), 7.41 (d,J=7.9, 1H), 7.55 (dd,J=8.2, 1H), 7.65-7.75 (m, 1H).
With ammonium acetate; acetic acid; In benzene; at 100℃;
Prep 38 (E)-ethyl 2-(6-chloro-2,3-dihydro-1 H-inden-1 -ylidene)-2-cyanoacetate (Prep38); <n="54"/>To a solution of <strong>[14548-38-0]6-chloro-indan-1-one</strong> ( commercially available, 16 g, 0.1 mol) in Benzene (500 ml), AcOH (160 ml) CH3COONH4 (80 g) and ethyl cyanoacetate (14.4 g, 0.13 mol) were added. The mixture was heated to 1000C and stirred overnight with a Dean stark water trap. Then ethyl acetate was added and the mixture washed with water. The residue was first purified by FC followed by crystallization from ethanol to obtain the title compound (16.2 g, y = 64.5%).1H NMR (DMSO) delta: 8.42 (1 H, s), 7.69-7.72 (1 H, d), 7.62-7.64 (1 H, d), 4.25-4.30 (2H, q), 3.46-3.48 (2H, t), 3.06-3.08 (2H, t), 1.27-1.31 (3H, t).
With ammonium acetate; acetic acid;piperidine; In toluene; for 18h;Heating / reflux;
6-Chloro-indanone (40g, 0.24 mol) was dissolved in toluene (400 mL). To the solution was added ethyl cyanoacetate (108.5g, 0.96 mol), ammonium acetate (18.5g, 0.24 mol), glacial acetic acid (28.8g, 0. 48mol) and piperidine (2.37 mL, 0.024 mol). The mixture was placed under nitrogen and heated to reflux for 18 hours. The mixture was then allowed to cool to room temperature. The mixture was washed with water, aquous sodium carbonate and then with brine. The separated organic phase was dried (MgS04), filtered and concentrated in vacuo. The product was triturated with diethyl ether and then filtered off. The product was washed with diethyl ether and then methanol. The product was air dried to a constant weight. Yield 36g, 57%.
Step 3; To a solution of borane-tetrahydrofuran (1.8 mL, 1.8 mmol, Aldrich, 1 M solution in THF) and (R) -MeCBS (0.3 mL, 0.3 mmol, Aldrich, 1 M solution in toluene) was added a solution of previous indanone (0.5 g, 3.0 mmol) in anhydrous tetrahydrofuran slowly over 30 min at room temperature. After complete addition, the reaction mixture was stirred for 10 min, quenched with 2N hydrochloric acid over 30 min. The reaction mixture was extracted with ether, dried, filtered and concentrated to afford 498 mg of (S)-6-chloroindan-l-ol.
Example 150; 5-((R)-6-Chloroindan-1-yloxy)quinazoline-2,4-diamine; [004231' Step 1; To a solution of borane-tetrahydrofuran (1.8 mL, 1.8 mmol, Aldrich, 1 M solution in THF) and (S) -MeCBS (0.3 mL, 0.3 mmol, Aldrich, 1 M solution in toluene) was added a solution of6-chloro-l-indanone (0.5 g, 3.0 mmol) in anhydrous tetrahydrofuran slowly over 30 min at room temperature. After complete addition, the reaction mixture was stirred for 10 min, quenched with 2N hydrochloric acid over 30 min. The reaction mixture was extracted with ether, dried, filtered and concentrated to afford 500 mg of (R)-6-chloroindan-l-ol.
With hydroxylamine hydrochloride; potassium carbonate; In methanol;
6--Chloro-1-indanone oxime may be prepared according to the protocol described in Example 1 for the preparation of 1-indanone oxime, starting from 32.4 g of <strong>[14548-38-0]6-chloro-1-indanone</strong>, 47.3 g of hydroxylamine hydrochloride, 47 g of potassium carbonate, 53 ml of distilled water and 530 ml of methanol. 33 g of expected product are obtained in the form of a yellow solid melting at 167 C. 6--Chloro-1-indanone may be prepared according to the process described by R. Sieka and W. Kellermann, Chem. Ber., 75, 1730 (1942).
(a) 2-Bromo-<strong>[14548-38-0]6-chloro-1-indanone</strong> A solution of 9.59 g (60.0 mmoles) of bromine in 20 ml of acetic acid ethyl ester is added dropwise to a solution of 10.0 g (60.0 mmoles) of <strong>[14548-38-0]6-chloro-1-indanone</strong> in 80 ml of acetic acid ethyl ester and 0.5 ml of 48% strength aqueous hydrobromic acid. After stirring for 3 hours, the reaction solution is concentrated to dryness, the residue is stirred with 50 ml of water and the precipitate is filtered off. The crude product of melting point 84-87 is recrystallized from petroleum ether 60/70 and gives the pure product of melting point 92-94 C.
6-Chloro-spiro-[indane(1,5')oxazolidine]-2',4'-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 8 6-Chloro-spiro-[indane(1,5')oxazolidine]-2',4'-dione Following the procedure of Examples 1 and 2, tbe title compound is prepared from <strong>[14548-38-0]6-chloro-indan-1-one</strong> (Bull. Soc. Chem. Fr. 1973, 3096).
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