* 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.
Reference：
[1] Canadian Journal of Chemistry, 1965, vol. 43, p. 498 - 509
9
[ 529-20-4 ]
[ 90050-59-2 ]
Yield
Reaction Conditions
Operation in experiment
21%
With aluminum (III) chloride; bromine In dichloromethane at 0 - 20℃; for 20.33 h;
Intermediate 6: 5-Bromo-2-methylbenzaldehydeTo a solution of 15.1 g (113 mmol) AICI3 in 30 ml_ CH2CI2 at O0C was added dropwise over 20 min 7.50 ml_ (64.8 mmol) of 2-methylbenzaldehyde followed by the dropwise addition of 3.35 ml_ (64.8 mmol) Br2 in 30 ml_ CH2CI2 <n="54"/>over 8 hrs at O0C. The solution was allowed to warm to room temperature over 12 hours then was poured over 50Og ice. This mixture was extracted with 400 ml_ CH2CI2 and the organics washed with 250 ml_ 1.0 N HCI (aq), 250 ml_ sat. NaHCO3 (aq) and 250 ml_ brine then dried over Na2SO4. The solution was concentrated then the resulting solid was recrystallized twice from 50 ml_ hexanes to give 2.92 g (21 percent) of 5-bromo-2-methylbenzaldehyde as an off-white solid: 1 H NMR (400 MHz, CDCI3). δ 10.21 (s, 1 H), 7.94 (s, 1 H), 7.57 (d, 1 H, J = 8.5 Hz), 7.16 (d, 1 H, J = 8.5 Hz), 2.64 (s, 3H.)
5%
With aluminum (III) chloride; bromine In dichloromethane at 0 - 20℃; for 18.5 h;
Example 15E 5-Bromo-2-methylbenzaldehyde 77.7 g (583 mmol) of aluminium trichloride are suspended in 200 ml of dichloromethane and cooled to 0° C. 40.0 g (333 mmol) of 2-methylbenzaldehyde are added dropwise over the course of 30 min. Then 53.2 g (333 mmol) of bromine are added at 0° C. over the course of 6 h, and the mixture is allowed to warm to RT and is stirred for 12 h. The reaction solution is added to 500 ml of ice-water. The aqueous phase is extracted several times with dichloromethane. The combined organic phases are washed successively with 2N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated in vacuo. Purification is by silica gel chromatography and subsequently by crystallization from cyclohexane. The precipitated product is filtered off. Yield: 3.2 g (5percent of theory) LC-MS (method 9): Rt=3.26 min MS (EI): m/z=199 (M+H)+
Reference：
[1] Journal of the American Chemical Society, 2000, vol. 122, # 29, p. 6935 - 6949
[2] Patent: WO2008/28118, 2008, A1, . Location in patent: Page/Page column 52-53
[3] Patent: US2007/99885, 2007, A1, . Location in patent: Page/Page column 23
[4] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 356
[5] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 356
[6] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 356
[7] Patent: EP2746301, 2014, A1, . Location in patent: Page/Page column
10
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[ 83647-40-9 ]
Reference：
[1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1645 - 1652
[2] Patent: WO2005/51911, 2005, A1, . Location in patent: Page/Page column 70
[3] Patent: WO2013/7650, 2013, A1, . Location in patent: Page/Page column 68;69
11
[ 529-20-4 ]
[ 2040-14-4 ]
Reference：
[1] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1594 - 1596
[2] Phytochemistry, 2013, vol. 96, p. 223 - 234
12
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[ 51725-82-7 ]
Reference：
[1] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7599 - 7608
[2] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7599 - 7608
Stage #1: at 25℃; for 0.5 h; Stage #2: With sodium tetrahydroborate In methanol; water at 0 - 25℃; for 1 h;
To a solution of 2-methylbenzaldehyde (10.0 g, 83.23 mmol) in MeOH at 25° C. was added methylamine (40 percent in H2O, 25.85 g, 332.9 mmol). The reaction mixture was stirred at 25° C. for 30 min after which time it was cooled to 0° C. and NaBH4 (6.30 g, 166.5 mmol) was added portion-wise. The reaction mixture was then warmed to 25° C. and stirred for an additional 1 hr. The solvent was removed under reduced pressure and water and CH2Cl2 were added. The organic layer was separated and washed with saturated NaHCO3 and brine. After drying over Na2SO4, organic phase was concentrated to afford desired methyl-(2-methyl-benzyl)-amine (10.49 g, 93.2percent) as an oil of sufficient purity for use in the next reaction: MS(APCI+) 136.3 m/z (M+H); H-NMR (CDCl3) δ 7.35-7.08 (m, 3 H), 3.73 (s, 2 H), 2.49 (s, 3 H), 2.34 (s, 3 H).
Reference：
[1] Patent: US2006/111422, 2006, A1, . Location in patent: Page/Page column 53
[2] Journal of the American Chemical Society, 1940, vol. 62, p. 910
[3] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 111
[4] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 390 - 401
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[ 874-33-9 ]
Reference：
[1] Organic Letters, 2011, vol. 13, # 4, p. 600 - 603
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7219 - 7222
20
[ 593-51-1 ]
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[ 874-33-9 ]
Reference：
[1] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
21
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[ 83647-40-9 ]
Reference：
[1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1645 - 1652
[2] Patent: WO2005/51911, 2005, A1, . Location in patent: Page/Page column 70
[3] Patent: WO2013/7650, 2013, A1, . Location in patent: Page/Page column 68;69
22
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[ 342417-01-0 ]
Reference：
[1] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1157 - 1166
23
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[ 873443-66-4 ]
Reference：
[1] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1157 - 1166
24
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[ 914299-79-9 ]
[ 138713-44-7 ]
Reference：
[1] Angewandte Chemie - International Edition, 2015, vol. 54, # 37, p. 10884 - 10888[2] Angew. Chem., 2015, vol. 54, p. 10884 - 10888,5
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Reference：
[1] European Journal of Medicinal Chemistry, 2015, vol. 99, # 1, p. 82 - 91
To a solution of 2-methylbenzaldehyde (10.0 g, 83.23 mmol) in MeOH at 25 C. was added methylamine (40 % in H2O, 25.85 g, 332.9 mmol). The reaction mixture was stirred at 25 C. for 30 min after which time it was cooled to 0 C. and NaBH4 (6.30 g, 166.5 mmol) was added portion-wise. The reaction mixture was then warmed to 25 C. and stirred for an additional 1 hr. The solvent was removed under reduced pressure and water and CH2Cl2 were added. The organic layer was separated and washed with saturated NaHCO3 and brine. After drying over Na2SO4, organic phase was concentrated to afford desired methyl-(2-methyl-benzyl)-amine (10.49 g, 93.2%) as an oil of sufficient purity for use in the next reaction: MS(APCI+) 136.3 m/z (M+H); H-NMR (CDCl3) delta 7.35-7.08 (m, 3 H), 3.73 (s, 2 H), 2.49 (s, 3 H), 2.34 (s, 3 H).
With sodium tetrahydroborate; water;
Step A: o-Tolualdehyde was converted to methyl-(2-methyl-benzyl)-amine via reductive amination using aqueous methyl amine and NaBH4. Methyl-(2-methyl-benzyl)-amine was then alkylated with 2-bromo-2'-acetonaphthone followed by reduction by NaBH4 to give 2-[methyl-(2-methyl-benzyl)-amino]-1-naphthalen-2-yl-ethanol as a clear, light yellow oil: 1H NMR (300 MHz, CDCl3) delta 7.78-7.87 (m, 4 H), 7.40-7.51 (m, 3 H), 7.14-7.30 (m, 4 H), 4.89 (dd, J=10.1, 3.9 Hz, 1 H), 3.71 (d, J=12.9 Hz, 1 H), 3.54 (d, J=12.9 Hz, 1 H), 2.70 (dd, J=12.3, 10.3 Hz, 1 H), 2.62 (dd, J=12.4, 3.9 Hz, 1 H), 2.41 (s, 3 H), 2.35 (s, 3 H); Cl MS m/z 306 [C21H23NO+H]+.
General procedure: 5-Chloro-2,3,4-trimethoxybenzaldehyde (1.01 g, 4.35 mmol) and 40% methylamine (0.20 g, 6.54 mmol) in methanol was stirred at room temperature for 30 min. Sodium borohydride (0.08 g, 2.18 mmol) was added at 0 C and was stirred for 1 h. The mixture was added water, methanol removed under reduced pressure and then extracted with dichloromethane three times. The organic layer was dried over Na2SO4, concentrated under reduced pressure to afford compound 9f in 89% yield.
7-methyl-2-(o-tolyl)quinazolin-4(3H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
58%
With sodium hydrogensulfite; In N,N-dimethyl acetamide; at 150℃;
General procedure: Sodium hydrogen sulfite (4 mmol) was added to a solution of anthranilamide 1 (2 mmol) and benzaldehyde 2 (2 mmol) in N,N- dimethylacetamide (5 mL). The mixture was heated under continuous stirring at 150 o C for 2-3 h and poured into ice water. The precipitate was then filtered, washed with water followed byethanol, and dried to yield the 2-arylquinazolinones 3-31.#10;#10;
2-bromo-7-(o-tolyl)-7,9,10,11-tetrahydroindazolo[3,2-b]quinazolin-8(5H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
93%
With iron(III) trifluoride; In neat (no solvent); at 80℃; for 0.333333h;Sonication; Green chemistry;
General procedure: To a 10 mL vessel was added 1H-indazol-3-amines (1, 1 mmol), aldehydes (2, 1 mmol), and 1,3-dicarbonyl compounds (3, 1 mmol), and FeF3 (10 mol %) the reaction was carried out under ultrasound (20 KHz, 80 C). The resulting solution was sonicated with a US probe for the time indicated in Table 2. After completion of the reaction, as indicated by TLC, reaction diluted with water precipitate product separated out by simple filtration washed with water and dried to afford the pure products 4. The FeF3 catalyst was dissolved in water and also recovered by evaporating the aqueous layer under reduced pressure.
General procedure: In a dark environment, a mixture of <strong>[711007-44-2]2,3-<strong>[711007-44-2]diaminobenzamide</strong></strong>(1.51 g, 10 mmol), PYTZ (20 mg), and ethanol (200 mL)was taken in an open pear-shaped bottle, stirred magneticallyat room temperature, and then aldehyde (10 mmol) wasadded slowly in 2 min. The bottle was exposed to visiblelight (Xenon, 10 A) under stirring condition. The reactionwas monitored by TLC. After the reaction completed, thereaction mixture was transferred to a three-neck bottle outsideof the photochemical reactor and air was introduced toensure that the intermediate was completely oxidized. Then,the solvent was evaporated in vacuum to 40 mL until thesolid appeared. The mixture was cooled down in an ice bathfor crystallization, filtration. The crude solid was recrystallizedfrom 25 mL ethanol (30 C) to get the target products.
5,5-dimethyl-2-(2-(o-tolyl)-1H-imidazol-5-yl)-2,5-dihydrothiazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
62%
With silica-gel-supported sulfuric acid; ammonium acetate; In neat (no solvent); at 130℃; for 3h;
General procedure: To a mixture of aldehyde (1 mmol), <strong>[551-16-6]6-aminopenicillinic acid</strong> (1 mmol), and ammonium acetate (3 mmol), SiO2*H2SO4 (0.025 g) was added and heated in an oil bath up to 130 C in appropriate times. After the completion of the reaction (TLC monitoring, EtOAc: hexane 10/90 v/v), the mixture was diluted in hot ethanol, solid was filtered, and products were purified by recrystallization in watery ethanol.
General procedure: A mixture of compound A (5 mmol) and corresponding benzaldehyde (5 mmol) in 10 mL ethanol was refluxed for 24 hours in a reaction flask wrapped up by silver paper. Upon the reactions completed (monitored by TLC), tawny solids were obtained through suction filtration. The precipitates were washed with ethanol (5 mLx3) and recrystallized from ethanol with 50-84% yields.
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