* 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 0 - 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.
88%
With thionyl chloride In dichloromethane
(a) To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0.279 mol) in 500 ml of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 ml (0.418 mol) of thionyl chloride, the mixture was stirred 10 h, at room temperature and the solvent was removed in vacuo. The residue was dissolved in 1000 ml of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was sitrred at room temperature for 1 h. The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2*200 ml). The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88percent) of 6-methoxy-1-indanone.
88%
With thionyl chloride In dichloromethane
(a) To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0,279 mol) in 500 mL of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 mL (0.418 mol) of thionyl chloride, the mixture was stirred 10 h at room temperature and the solvent was removed in vacuo. The residue was dissolved in 1000 mL of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was stirred at room temperature for 1 h. The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2*200 mL). The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88percent) of 6-methoxy-1-indanone.
Reference：
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[2] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 5, p. 470 - 475
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
[4] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[5] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1741 - 1745
[6] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
[7] Journal of the American Chemical Society, 1945, vol. 67, p. 1853
[8] Journal of the American Chemical Society, 1949, vol. 71, p. 1092,1095
[9] Yakugaku Zasshi, 1956, vol. 76, p. 163,165, 166[10] Chem.Abstr., 1956, p. 13850
[11] Angewandte Chemie, 1954, vol. 66, p. 435
[12] Monatshefte fuer Chemie, 1978, vol. 109, p. 405 - 419
[13] Chemische Berichte, 1969, vol. 102, p. 3656 - 3665
[14] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 4, p. 687 - 695
[15] Heterocycles, 1988, vol. 27, # 9, p. 2213 - 2217
[16] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 4, p. 407 - 412
[17] Patent: US5569655, 1996, A,
[18] European Journal of Medicinal Chemistry, 2010, vol. 45, # 1, p. 25 - 37
[19] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[20] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5788 - 5793
[21] Patent: US5554620, 1996, A,
3
[ 557775-38-9 ]
[ 13623-25-1 ]
Yield
Reaction Conditions
Operation in experiment
75%
With trifluorormethanesulfonic acid In chloroform at 50℃;
General procedure: The 4-nitrophenylamides (10-16) also underwent very efficient intramolecular reactions (Table 1). For example, amide 10 (R═H) provided 1-indanone (17) in 90percent yield upon reaction with CF3SO3H in CHCl3. The 4-nitroaniline by-product may be isolated with up to 90percent recovery. Other acids were studied in this conversion (H2SO4, CF3CO2H, AlCl3, HY-zeolite, Sc(OTf)3), but none successfully converted 10 to the indanone 17. Amides 11-13 also gave the corresponding substituted 1-indanones (18-20) in good yields. The amide 10′ (below), also gave the corresponding substituted 1-indanone 17′ (below), in 68percent yield (other isomers were also obtained).
Reference：
[1] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5788 - 5793
[2] Patent: US2013/267712, 2013, A1, . Location in patent: Paragraph 0038-0039
4
[ 201230-82-2 ]
[ 3989-14-8 ]
[ 13623-25-1 ]
Reference：
[1] Journal of Organic Chemistry, 1993, vol. 58, # 20, p. 5386 - 5392
5
[ 5111-69-3 ]
[ 13623-25-1 ]
[ 5111-70-6 ]
Reference：
[1] Tetrahedron Letters, 1998, vol. 39, # 11, p. 1385 - 1388
[2] Synthesis, 1994, # 9, p. 915 - 916
[3] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8767 - 8772
[4] European Journal of Organic Chemistry, 2003, # 3, p. 578 - 586
[5] ChemCatChem, 2013, vol. 5, # 1, p. 126 - 129
6
[ 62803-47-8 ]
[ 74-88-4 ]
[ 13623-25-1 ]
Reference：
[1] Journal of Organic Chemistry, 2018, vol. 83, # 1, p. 452 - 458
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2436 - 2441
7
[ 123-11-5 ]
[ 13623-25-1 ]
Reference：
[1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[3] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
[4] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[5] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
8
[ 1929-29-9 ]
[ 13623-25-1 ]
[ 146301-02-2 ]
[ 13577-08-7 ]
Reference：
[1] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
[2] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
[3] Journal of Organic Chemistry, 1993, vol. 58, # 3, p. 556 - 559
9
[ 3469-09-8 ]
[ 13623-25-1 ]
Reference：
[1] Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 5875 - 5880
10
[ 15893-42-2 ]
[ 13623-25-1 ]
Reference：
[1] Journal of Organic Chemistry, 1984, vol. 49, # 14, p. 2517 - 2520
[2] Journal of Organic Chemistry, 1970, vol. 35, p. 647 - 651
[3] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
11
[ 943-89-5 ]
[ 13623-25-1 ]
Reference：
[1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
Stage #1: With aluminum (III) chloride In toluene at 20℃; for 1 h; Reflux Stage #2: With water In toluene
To a stirred suspension of aluminum chloride (5.3 g, 39.7 mmol) in toluene (75 mL) was slowly added 6-methoxy-l-indanone (2.5 g, 15.4 mmol) at room temperature under a nitrogen atmosphere. The residual 6-methoxy-l-indanone which remained in the powder addition funnel was rinsed into the reaction mixture with toluene (25 mL). The reaction mixture was heated at reflux for 1 h. The reaction mixture was allowed to cool at room temperature and slowly poured into ice-water. The mixture was transferred to a separatory funnel with the aid of ethyl acetate. The layers were separated and the organic phase was washed with water (2 times) followed by saturated sodium chloride, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give 1.5 g (66percent) of 6-hydroxy-2,3-dihydro-lH-inden-l-one as a pale tan solid. 1H NMR (400 MHz, DMSO-J6): δ 9.72 (s, IH), 7.36 (d, J = 8 Hz, IH), 7.07 (dd, J = 8, 3 Hz, IH), 6.90 (d, J = 3 Hz, IH), 2.94 (m, 2H), 2.58 (m, 2H). ES-LCMS m/z 149 (M + H)+.
Reference：
[1] Organic Preparations and Procedures International, 2009, vol. 41, # 4, p. 309 - 314
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 7, p. 1068 - 1083
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 20, p. 5665 - 5670
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1675 - 1678
[5] Chemical Communications, 2011, vol. 47, # 22, p. 6290 - 6292
[6] Organic and Biomolecular Chemistry, 2017, vol. 15, # 35, p. 7374 - 7379
[7] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 4, p. 687 - 695
[8] Tetrahedron Letters, 1997, vol. 38, # 50, p. 8749 - 8752
[9] Patent: WO2009/5998, 2009, A1, . Location in patent: Page/Page column 266
[10] European Journal of Organic Chemistry, 2003, # 9, p. 1681 - 1686
[11] Patent: US6166006, 2000, A,
[12] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155
[13] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 487 - 497
[14] Patent: US2820817, 1954, ,
19
[ 13623-25-1 ]
[ 22246-05-5 ]
Reference：
[1] Patent: WO2012/3418, 2012, A2,
20
[ 13623-25-1 ]
[ 3469-08-7 ]
Reference：
[1] Journal of Organic Chemistry, 1961, vol. 26, p. 4859 - 4866
With copper(ll) bromide In chloroform; ethyl acetate for 1h; Heating;
44%
With copper(ll) bromide In ethyl acetate for 4h; Heating / reflux;
6; 12; 3
20 g (123 mmol) of indanone Il are dissolved in 250 ml_ of ethyl acetate. 33.1 g (148 mmol) of copper bromide are added at once and it is heated under reflux for 4 h with strong stirring. During the stirring a change in colour is observed in the crude from black to green, indicating the copper reduction. Once the reaction has finished it is allowed to cool and filtered over Celite. The filtrate is evaporated to dryness under low pressure. 27 g are obtained of a residue that is purified by column chromatography, using DCM as an eluant. 16.6 g (Yield = 44%) are thus obtained of a yellow solid X.HPLC-MS: Purity 93.7%, M+1 =242
With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃;
With copper(ll) bromide In ethyl acetate at 20℃; Reflux;
57.a
To a stirred suspension of copper(II) bromide (16.6 g, 74.3 mmol) in ethyl acetate (50 mL) at reflux was added, dropwise, over a period of 25 min a solution of 6-methoxy- 1-indanone (6.2 g, 38.2 mmol) in chloroform (50 mL) under a nitrogen atmosphere. The reaction mixture was heated at reflux for 1 h. The oil bath was removed and the reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was filtered and the off-white solid was washed with chloroform. The filtrate was concentrated to give the crude product as a turbid liquid. Ethyl acetate was added to the crude product and the cloudy solution was applied to a silica column. The crude product was purified by flush chromatography with hexanes: ethyl acetate (9:1) to give the desired product. The product was dissolved in ethanol and the solution was concentrated to give 8.6 g (93%) of 2-bromo-6-(methyloxy)-2,3-dihydro-lH- inden-1-one as a pale tan solid. 1H NMR indicated the product contained 6-methoxy- 1-indanone (approximately 5% by weight). The product was used without further purification. 1H NMR (400 MHz, CDCl3): δ 7.33 (m, IH), 7.25 (m, 2H), 4.66 (dd, J = 7, 3 Hz, IH), 3.84 (s, 3H), 3.76 (dd, J = 18, 7 Hz, IH), 3.34 (dd, J = 18, 3 Hz, IH). AP-LCMS m/z 241 (M + H)+.
With copper(ll) bromide In chloroform; ethyl acetate Reflux;
Stage #1: dimethyl zinc(II) With titanium tetrachloride In dichloromethane at -40℃; for 0.5h; Inert atmosphere;
Stage #2: 6-methoxy-2,3-dihydro-1H-inden-1-one In dichloromethane at -40 - 20℃; Inert atmosphere;
23.I Step I: Preparation of 6-methoxy-1,1-dimethyl-2,3-dihydro-1H-indene (23-1)
TiCl4 (2.2 mL, 0.02 mmol) was dissolved in 20 mL anhydrous dichloromethane and added with Me2Zn (80 mL, 0.08 mmol) at -40 °C with stirring under the nitrogen protection. The mixture was kept at the temperature and stirred for 30 min, 6-methoxy-1-indone (1.76 g, 0.01 mmol) dissolved with 5 mL dichloromethane was added and the mixture was slowly raised to room temperature and reacted overnight. To the reaction solution, 10 mL anhydrous methanol was slowly dripped to quench the reaction, and then dichloromethane and saturated NH4Cl solution were added for dilution and extraction. The organic phase was washed with saturated NH4Cl solution twice, and the aqueous phase was washed twice with dichlormethane. The organic phases were combined, dried and concentrated to afford an oily liquid (2.10 g, 72%).
71%
With titanium tetrachloride In dichloromethane; toluene
71%
With titanium tetrachloride In dichloromethane; toluene
71%
With titanium tetrachloride In dichloromethane; toluene
With titanium tetrachloride In dichloromethane; toluene at -40 - 20℃; for 3h;
Stage #1: dimethyl zinc(II) With titanium tetrachloride In dichloromethane; toluene at -40℃; for 0.5h;
Stage #2: 6-methoxy-2,3-dihydro-1H-inden-1-one In dichloromethane; toluene at -40 - 20℃; for 3h;
82.1
A stirred, cooled (-40° C.) solution of titanium tetrachloride in anhydrous dichloromethane (1M, 20 mL) under N2, is treated with a solution of dimethyl zinc (2M, 30 mL) in toluene. After 30 min, a solution of 6-methoxy-indan-1-one (1.62 g, 10 mmol) in dichloromethane (anhydrous, 10 mL) is added via syringe. After addition, the reaction is warmed to rt and stirring is continued for 3 h. The reaction mixture is then cooled to -40° C. and cautiously quenched with methanol (1 mL). The mixture is diluted with DCM and saturated aqueous ammonium chloride solution. The phases are separated and the aqueous phase is extracted with dichloromethane (2×20 mL). The combined organic phases are dried over Na2SO4, filtered and evaporated in vacuo to afford 6-methoxy-1,1-dimethyl-indan as an oil: 1H NMR (400 MHz, CDCl3) δ 7.19-7.20 (m, 1H), 7.10-7.12 (m, 1H), 6.69-6.68 (m, 1H), 3.82 (s, 3H), 2.82 (t, 2H, J=7.2 Hz), 1.92 (t, 2H, J=7.2 Hz), 1.24 (s, 6H).
With sodium azide; methanesulfonic acid; In chloroform; at 0 - 20℃; for 3h;
To a mixture of 6-Methoxy-l-indanone (15 g, 92.6 mmol), sodium azide (26.7 g, 277.8 mmol), in CHCl3 was added methane sulfonic acid (60 g, 926 mmol) via addition funnel at 0 0C. Reaction mixture was warm to room temperature. Stirring was continued for 3 hr, then poured into cold water. The organics were extracted with methylene chloride and washed with water, sat. NaCl and dried over Na2SO4, Organic solution was concentrated in vacuo and the residue was purified with silica gel eluting EPO <DP n="77"/>with 20 % EtOAc/Hexane to give the title compound as a yellow solid (10.5 g, 63 %). MS (ES) m/z 178.1.
With sodium azide; trichloroacetic acid; at 70℃; for 12h;
To a heated solution of 6-methoxy-indan-1-one (3g) in trichloroacetic acid (30g) is added sodium azide (1. 8G) at 70C and, and the mixture is maintaining with stirring for 12HR. The reaction mixture is diluted with ice water and neutrized with potassium carbonate, and extracted with ethyl acetate (TWICE). The organic layer is successively washed with water and saturated NaClaq, dried over MgS04, concentrated in vacuo. The crude product is purified by column chromatography to provide the title compound; 1 H NMR (CI3, 6 (ppm) ); 2.86 (dd, 2H), 3.45-3. 50 (m, 2H), 3.78 (s, 3H), 6.36 (brs, 1 H), 6.92-6. 95 (m, 1 H), 7.06 (d, 1 H), 7.52 (d, 1H).
1-(Cyclopropylcarbonyl)-4-(6-methoxy-indan-1-yl)piperazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium hydroxide; sodium borohydrid;titanium(IV) isopropylate; In ethanol;
Example 15 1-Cyclopropylcarbonyl-4-(6-methoxy-indan-1-yl)piperazine An intimate mixture of 6-methoxy-1-indanone (1.6 g, 10 mmol), 1-cyclopropanecarbonylpiperazine (1.5 g, 10 mmol) and titanium(IV) isopropoxide (4 mL, 12 mmol) was heated on the steam bath for 10 minutes. Additional titanium isopropoxide (1 mL, 3 mmol) was added and the mixture stirred for 20 hr. The material was dissolved in ethanol and sodium borohydride added (0.9 g, 22 mmol). After stirring for 1 hr the solution was heated to reflux and more sodium borohydride (0.9 g, 22 mmol) added. When solution had occurred 15% NaOH solution (50 mL) was added. The insoluble material was removed and discarded. The solution was concentrated in vacuo and the residue mixed with ether. The mixture was washed with water and 1N HCl solution. The acid washes were made basic and the mixture was extracted with ether to give the product as an oil which was converted to the fumarate salt and crystallized from acetone to give the salt (1.8 g).
4-(6-Methoxy-indan-1-yl)-1-(2-methyl-propanoyl)piperazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium borohydrid
16 1-(2-Methylpropionyl)-4-(6-methoxy-indan-1-yl)piperazine
Example 16 1-(2-Methylpropionyl)-4-(6-methoxy-indan-1-yl)piperazine The title compound was prepared by the above procedure using 6-methoxy-1-indanone (3.2 g, 20 mmol), 1-(2-methylpropionyl)piperazine (3.0 g, 20 mmol), titanium(IV) isopropoxide (8 mL, 24 mmol) and sodium borohydride (2.7 g, 67 mmol) to give 2.2 g of product as the fumarate salt.
With hydrogenchloride In methanol at 20 - 40℃; for 2h;
45B Example 45B: 2-(hydroxyimino)-6-methoxy-2,3 -dihydro- 1H-inden- 1-one (B-45)
j00362j To a solution of 6-methoxyindan-1-one (1.0 g, 6.2 mmol) in methanol (20 mL) at room temperature was added hydrochloric acid (1.0 mL, 12 mmol) and isoamyl nitrite (1.6 g, 14 mmol). The solution was stirred at 40 °C for 2 hours, then filtered and concentrated in vacuo to give compound B-45 (0.80 g, 68% yield) as a yellow solid. LCMS (B): tR=0.592 mi, (ES+) m/z (M+H)+ =192.1.
In methanol
P.1.1.a Method 1
a) 6-methoxy-1-indanone (8.6 g, 53 mmol) (see J. Org. Chem., 35, 647 (1970)) was added to methanol (500 ml), then heated to 40°C, and isoamyl nitrite (15 ml, 110 mmol) and concentrated hydrochlolic acid (8.5 ml) were added thereto followed by stirring for 2 hours. The crystals that deposited on cooling the reaction mixture were filtered to obtain 6-methoxy-2-oxyimino-1-indanone (5.5 g, 29 mmol) having the following physical properties: 1H NMR (400 MHz, DMSO-d6): δ 3.69 (2H, s), 3.83 (3H, s), 7.21 (1H, d, J = 2Hz), 7.32 (1H, dd, J = 2Hz, 8 Hz), 7.53 (1H, d, J = 8 Hz), 12.58 (1H, br. s).
In methanol
P.74.t.o.189.a Method 1
a) 6-methoxy-1-indanone (8.6 g, 53 mmol) (see J. Org. Chem., 35, 647 (1970)) was added to methanol (500 ml), then heated to 40°C, and isoamyl nitrite (15 ml, 110 mmol) and concentrated hydrochlolic acid (8.5 ml) were added thereto followed by stirring for 2 hours. The crystals that deposited on cooling the reaction mixture were filtered to obtain 6-methoxy-2-oxyimino-1-indanone (5.5 g, 29 mmol) having the following physical properties: 1H NMR (400 MHz, DMSO-d6): δ 3.69 (2H, s), 3.83 (3H, s), 7.21 (1H, d, J = 2Hz), 7.32 (1H, dd, J = 2Hz, 8 Hz), 7.53 (1H, d, J = 8 Hz), 12.58 (1H, br. s).
l-Cyclopropylidene-6-methoxy-2,3-dihydro-1H-indene (H10.2). NaH(1.5 g, 62 mmol) was added to a suspension of cyclopropyltriphenyl-phosphonium bromide (24 g, 62 mmol) (commercially available from Sigma-Aldrich, St. Louis, MO, USA) in THF (100 mL), and the resulting mixture was stirred at room temperature for 2 hours. Then, 6-methoxy-1-indanone (H10.1) (Oakwood Products, Inc.) (5.00 g, 31 mmol) and tris(2-(2-methoxyethoxy)ethyl)amine (commercially available from Sigma- Aldrich, St. Louis, MO, USA) (1.1 mL, 3.1 mmol) were added slowly. The resulting mixture was stirred at room temperature for 10 minutes and then at 62C for 4 hours. The reaction mixture was concentrated and purified by chromatography (silica gel, eluting with 1 :9 EtOAc/hexane) to provide H10.2 (4.53 g, 79% yield) as a solid. MS ESI (pos.) M/E: 187.1 (M+H).
Reference Example 82 1-(2,4-dichlorophenyl)-6-methoxyindan-1-ol To a mixture of magnesium (3.89 g, 160 mmol) and THF (100 mL) was added dropwise a solution of <strong>[1193-72-2]1-<strong>[1193-72-2]bromo-2,4-dichlorobenzene</strong></strong> (4.18 g, 18.5 mmol) in THF (50 mL), and the mixture was stirred at room temperature for 2 hr to give a Grignard reagent. Then, a solution of 6-methoxyindan-1-one (10.0 g, 61.7 mmol) in THF (50 mL) was added dropwise thereto under ice-cooling, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was poured into a mixture of ice and ammonium chloride, and the mixture was extracted with diethyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (12.6 g, yield 66%) as an oil. 1H-NMR (CDCl3) delta: 2.29 - 2.42 (1H, m), 2.57 (1H, s), 2.88 (2H, q, J = 10.2 Hz), 3.01 - 3.20 (1H, m), 3.73 (3H, s), 6.55 (1H, d, J = 2.3 Hz), 6.87 (1H, dd, J = 8.3, 2.3 Hz), 7.17 - 7.25 (2H, m), 7.37 (1H, d, J = 2.3 Hz), 7.53 (1H, d, J = 8.7 Hz).
Reference Example 76 1-(2,5-dichlorophenyl)-6-methoxyindan-1-ol To a solution of <strong>[1435-50-3]1-bromo-2,5-dichlorobenzene</strong> (4.18 g, 18.5 mmol) in THF (25 mL) was added dropwise 1.6 M n-butyllithium hexane solution (13.8 mL, 22.1 mmol) at -78C, and the mixture was stirred for 30 min. Then, a solution of 6-methoxyindan-1-one (2.00 g, 12.3 mmol) in THF (15 mL) was added dropwise, and the mixture was stirred for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (1.95 g, yield 51%) as an oil. 1H-NMR (CDCl3) delta: 2.29 - 2.42 (1H, m), 2.52 (1H, s), 2.79 - 3.00 (2H, m), 3.04 - 3.23 (1H, m), 3.73 (3H, s), 6.53 (1H, d, J = 2.4 Hz), 6.87 (1H, dd, J = 8.3, 2.4 Hz), 7.16 - 7.30 (3H, m), 7.70 (1H, d, J = 2.3 Hz).
Multi-step reaction with 2 steps
1: hydrogenchloride / water; methanol / 2 h / 40 °C
2: hydrogenchloride; trichlorophosphate; phosphorus pentoxide / 2 h / 0 - 30 °C
Multi-step reaction with 2 steps
1.1: hydrogenchloride / diethyl ether / 3 h / 0 °C
1.2: 3 h / 20 °C
2.1: hydrogenchloride; phosphorus pentachloride / 19 h / 0 - 60 °C
Multi-step reaction with 2 steps
1: hydrogenchloride / methanol / 2 h / 20 - 40 °C
2: phosphorus pentachloride; trichlorophosphate; hydrogenchloride / 12 h / 0 - 80 °C
Multi-step reaction with 2 steps
1: isopentyl nitrite; hydrogenchloride / water / 2 h / 40 °C
2: hydrogenchloride; trichlorophosphate; phosphorus pentachloride / 18 h / 0 - 30 °C
2-(4-(4-ethylpiperazin-1-yl)benzylidene)-6-methoxy-2,3-dihydro-1H-inden-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
With potassium hydroxide In methanol at 20℃; for 48h;
4.1.1.4. 5-Methoxy, 6-methoxy or 5,6-dimethoxy-2-(4-substituedbenzilidene)-2,3-dihydro-1H-inden-1-one derivatives(15-38).
General procedure: A mixture of appropriate indan-1-one derivative(2 mmol), benzaldehyde derivative (2 mmol) and potassium hydroxide(2 mmol, 0.112 g) in methanol (10 mL) was stirred at roomtemperature for 48 h. The resulting colored solid was filtered, driedand crystallized from EtOH [63].
2-(4-(pyrrolidin-1-yl)benzylidene)-6-methoxy-2,3-dihydro-1H-inden-1-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
With potassium hydroxide; In methanol; at 20℃; for 48h;
General procedure: A mixture of appropriate indan-1-one derivative(2 mmol), benzaldehyde derivative (2 mmol) and potassium hydroxide(2 mmol, 0.112 g) in methanol (10 mL) was stirred at roomtemperature for 48 h. The resulting colored solid was filtered, driedand crystallized from EtOH [63].
3-(4-chlorophenyl)-8-methoxy-5H-indeno[1,2-c]pyridazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With hydrazine hydrate; DBN; In water; at 25℃; for 4h;Green chemistry;
General procedure: To a stirred mixture of indanone (1 mmol), arylglyoxalmonohydrate (1 mmol), and DBN (25 mol-%) in water (5 mL) was added hydrazine hydrate (3 mmol) at room temperature. The suspension was then stirred for 2-4 h, as shown in Table 2. After the appropriate time, the heterogeneous mixture was filtered and the product recrystallised from ethanol.
3-(3-bromophenyl)-8-methoxy-5H-indeno[1,2-c]pyridazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
72%
With hydrazine hydrate; DBN; In water; at 25℃; for 4.0h;Green chemistry;
General procedure: To a stirred mixture of indanone (1 mmol), arylglyoxalmonohydrate (1 mmol), and DBN (25 mol-%) in water (5 mL) was added hydrazine hydrate (3 mmol) at room temperature. The suspension was then stirred for 2-4 h, as shown in Table 2. After the appropriate time, the heterogeneous mixture was filtered and the product recrystallised from ethanol.
Stage #1: 6-methoxy-2,3-dihydro-1H-inden-1-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
Chemistry
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