* 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 trichlorophosphate In <i>N</i>-methyl-acetamide; water
Preparation 35 3-Formyl-1 H -indole-5-carbonitrile Phosphoryl chloride (4.24ml, 45.48mmol) was added dropwise to dimethylformamide (3.52ml, 45.48mmol) and stirred for 30mins at room temperature. A solution of 1H-indole-5-carbonitrile (5.39g, 37.9mmol) in dimethylformamide (10ml) was added dropwise. A solid precipitated, further dimethylformamide (10ml) was added to aid stirring and the reaction mixture was then stirred at room temperature for 3hr. Water was added to quench the reaction mixture which was then stirred for 18hr. The stirring was stopped and the reaction mixture was left to stand, after 24hr a pink solid had precipitated in the organic layer. The layers were separated and organic layer filtered, washed with water and dried to give the desired product (5.44g, 84percent). 1H NMR (DMSO)δ 7.60-7.80 (m, 2H), 8.20-8.30 (m, 2H), 10.00 (s, 1H), 12.20-12.35 (s, br, 1H).
75%
With sodium hydroxide; trichlorophosphate In <i>N</i>-methyl-acetamide
EXAMPLE 1 Trans-2-[5-Cyanoindol-3-yl]-1-(N,N-dimethylaminomethyl)cyclopropane Phosphorus oxychloride (10.9 ml, 117 mmol) was added dropwise over 30 min to anhydrous dimethylformamide (50 ml) that was maintained at 10-20° C. (internal temperature). The resulting mixture was stirred for 30 min and then chilled to 0° C. A solution of commercially available 5-cyanoindole (15 g, 106 mmol) in anhydrous dimethylformamide (30 ml) was added over 10 min. The ice bath was removed and the solution was allowed to warm to room temperature. After 2 h, a very thick paste resulted. The off-white paste was carefully quenched with ice chips. An aqueous solution of sodium hydroxide (2.12 g NaOH/100 ml H2O) was added. After a mild exotherm, a clear yellow solution resulted. The solution was poured into water (~400 ml) and a fine solid immediately precipitated. The mixture was filtered through a 600 ml glass fritted funnel of medium porosity. The yellow filtrate was diluted with an equal volume of water and left to stand for 16 h. A yellow precipitate was collected by vacuum filtration. The solid was dried overnight under vacuum to afford 13.6 g (75percent yield) of (5-cyanoindol-3-yl)carboxaldehyde: 1H NMR (500 MHz, DMSO-d6) 12.58 (1 H, br s,), 10.00 (1 H, s), 8.51 (1 H, d, J=3.1 Hz), 8.46 (1 H, d, J=0.6 Hz), 7.22 (1 H, dd, J=8.6, 0.5 Hz), 7.64 (1 H, dd, J=8.5, 1.6 Hz); MS m/e 171 (M+H)+.
Reference：
[1] Patent: EP997474, 2000, A1,
[2] Patent: US6180627, 2001, B2,
[3] Patent: US2003/73849, 2003, A1,
[4] Organic Process Research and Development, 2008, vol. 12, # 2, p. 168 - 177
2
[ 15861-24-2 ]
[ 110-18-9 ]
[ 17380-18-6 ]
Yield
Reaction Conditions
Operation in experiment
52%
With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; for 36 h; Schlenk technique; Sealed tube
General procedure: Under air, a 20 mL of Schlenk tube equipped with a stir bar was charged with indole 1 (0.2 mmol, 1 equiv),TMEDA (75 µL, 0.5 mmol, 2.5 equiv), Na2CO3 (42.4 mg, 0.4mmol, 2.0 equiv), 1,4-dioxane (0.5 mL) and H2O (100 µL). Then I2 (101.5 mg, 0.4 mmol, 2.0 equiv) was added and the tube was sealed with a rubber plug and charged with O2. The reaction mixture was stirred at 100 °C for 36 h in oil bath. After cooling to room temperature, the resultant mixture was evaporated with EtOAc (20 mL) under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the products.
POCI3 (3.6 mL, 38.68 mmol) was added to DMF (l 6.5 mL) dropwise at 0 °C- 10 °C. The resulting mixture was stirred for 30 minutes, cooled to 0 °C, and a solution of Intermediate Z (5.0 g, 35.17 mmol) in DMF (10.0 mL) was added over15 minutes. After the addition was complete, the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was quenched with ice (25 g), poured into water (50 mL), and NaOH (1.5g) was added. The mixture was filtered, and the yellow colored filtrate was diluted with water (100 mL) and left to stand at room temperature for 20 hours. The solid was then filtered and dried to affordIntermediate AA (1.5 g, 62percent) as a yellow solid. 1H NMR (DMSO-c3/4: δ 12.59 (bs, 1H), 10.00 (s, 1H), 8.52 (s, 1 H), 8.51 (s, 1H), 7.71 (s, J = 8.29 Hz; 1H), 7.65 (d, J = 8.70 Hz; 1H). Mass (M-H): 169.1
Reference：
[1] Organic Letters, 2013, vol. 15, # 17, p. 4330 - 4333
[2] Chemical Biology and Drug Design, 2011, vol. 78, # 5, p. 864 - 868
[3] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 24, p. 5696 - 5705
[4] MedChemComm, 2018, vol. 9, # 11, p. 1882 - 1890
[5] Organic Letters, 2005, vol. 7, # 13, p. 2651 - 2654
[6] Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6023 - 6034
[7] Patent: WO2011/47156, 2011, A1, . Location in patent: Page/Page column 57-58
[8] Farmaco, 1994, vol. 49, # 6, p. 443 - 448
[9] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 1, p. 81 - 86
[10] Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2843 - 2857
[11] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1793 - 1798
[12] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7274 - 7277
[13] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 1, p. 307 - 310
[14] Patent: EP1859798, 2015, B1, . Location in patent: Paragraph 0160
[15] Organic and Biomolecular Chemistry, 2018, vol. 16, # 36, p. 6647 - 6651
4
[ 15861-24-2 ]
[ 298-12-4 ]
[ 17380-18-6 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 20, p. 3707 - 3710
5
[ 100846-24-0 ]
[ 468717-17-1 ]
[ 17380-18-6 ]
Reference：
[1] Patent: US2003/73849, 2003, A1,
6
[ 17380-18-6 ]
[ 73396-90-4 ]
Reference：
[1] Chemistry - A European Journal, 2014, vol. 20, # 24, p. 7492 - 7500
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11881 - 11885[3] Angew. Chem., 2014, vol. 126, # 44, p. 12075 - 12079,5
7
[ 24424-99-5 ]
[ 17380-18-6 ]
[ 914348-93-9 ]
Yield
Reaction Conditions
Operation in experiment
0.379 g
With dmap In acetonitrile at 20℃;
General procedure: To a solution of an appropriate indole, azaindole or alternative heterocycles (1.0 eq) and di-ferf-butyl dicarbonate (1eq. to 2 eq., more in particular 1.2 eq) in acetonitrile was added DMAP (0.1 to 0.5 eq. more in particular 0.1 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with a saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The BOC-protected compound was used in the next step without further purification.
With sodium hydroxide; trichlorophosphate; In N,N-dimethyl-formamide;
EXAMPLE 1 Trans-2-[5-Cyanoindol-3-yl]-1-(N,N-dimethylaminomethyl)cyclopropane Phosphorus oxychloride (10.9 ml, 117 mmol) was added dropwise over 30 min to anhydrous dimethylformamide (50 ml) that was maintained at 10-20 C. (internal temperature). The resulting mixture was stirred for 30 min and then chilled to 0 C. A solution of commercially available 5-cyanoindole (15 g, 106 mmol) in anhydrous dimethylformamide (30 ml) was added over 10 min. The ice bath was removed and the solution was allowed to warm to room temperature. After 2 h, a very thick paste resulted. The off-white paste was carefully quenched with ice chips. An aqueous solution of sodium hydroxide (2.12 g NaOH/100 ml H2O) was added. After a mild exotherm, a clear yellow solution resulted. The solution was poured into water (~400 ml) and a fine solid immediately precipitated. The mixture was filtered through a 600 ml glass fritted funnel of medium porosity. The yellow filtrate was diluted with an equal volume of water and left to stand for 16 h. A yellow precipitate was collected by vacuum filtration. The solid was dried overnight under vacuum to afford 13.6 g (75% yield) of (5-cyanoindol-3-yl)carboxaldehyde: 1H NMR (500 MHz, DMSO-d6) 12.58 (1 H, br s,), 10.00 (1 H, s), 8.51 (1 H, d, J=3.1 Hz), 8.46 (1 H, d, J=0.6 Hz), 7.22 (1 H, dd, J=8.6, 0.5 Hz), 7.64 (1 H, dd, J=8.5, 1.6 Hz); MS m/e 171 (M+H)+.
62%
With trichlorophosphate; at 0 - 26℃; for 3h;
POCI3 (3.6 mL, 38.68 mmol) was added to DMF (l 6.5 mL) dropwise at 0 C- 10 C. The resulting mixture was stirred for 30 minutes, cooled to 0 C, and a solution of Intermediate Z (5.0 g, 35.17 mmol) in DMF (10.0 mL) was added over15 minutes. After the addition was complete, the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was quenched with ice (25 g), poured into water (50 mL), and NaOH (1.5g) was added. The mixture was filtered, and the yellow colored filtrate was diluted with water (100 mL) and left to stand at room temperature for 20 hours. The solid was then filtered and dried to affordIntermediate AA (1.5 g, 62%) as a yellow solid. 1H NMR (DMSO-c¾: delta 12.59 (bs, 1H), 10.00 (s, 1H), 8.52 (s, 1 H), 8.51 (s, 1H), 7.71 (s, J = 8.29 Hz; 1H), 7.65 (d, J = 8.70 Hz; 1H). Mass (M-H): 169.1
Example 23 3-Formyl-5-cyano-1H-indole Add phosphorous oxychloride (11.76 g, 76.67 mmol) dropwise to DMF (24.3 ml) wile maintaining the temperature at less than 10C. Warm to ambient temperature and stir for 15 minutes at ambient temperature. Add dropwise 5-cyanoindole (10.00 g, 70.34 mmol) as a solution in DMF (30 ml) while keeping the temperature below 35. After 1 hour, pour the reaction mixture into ice/water (300 ml) and then add 5N NaOH (54 ml) with stirring. Add slowly an additional amount of 5N NaOH (19.7 ml) and then heated to 90 for 1 minute and then cooled to ambient temperature to give a precipitate. Filter the precipitate and washed with water and dry to give the title compound: mp 248-250 C. MS (ACPI): m/e 171.0 (M+1). Analysis for C10H6N2O: Calcd: C, 70.58; H, 3.55; N, 16.46; found: C, 70.41; H, 3.53; N, 16.33.
p-Toluenesulfonyl chloride (15.2 g, 79.5 mmol) was added to a solution of <strong>[17380-18-6](5-cyanoindol-3-yl)carboxaldehyde</strong> (13.5 g, 79.5 mmol) and triethylamine (12.2 ml, 87.5 mmol) in anhydrous dichloromethane (250 ml). The mixture was left to stir for 24 h at room temperature. The solid precipitate was collected using a Buchner funnel and washed with ethanol. The white solid was dried under vacuum to afford 16.85 g (65% yield) of [5-cyano-1-(p-toluenesulfonyl)indol-3-yl]carboxaldehyde: mp 243 C. (dec.); 1H NMR (400 MHz, DMSO-d6) 10.09 (1 H, s), 9.07 (1 H, s), 8.49 (1 H, d, J=1.1 Hz), 8.16 (1 H, dd, J=8.6, 0.3 Hz), 8.06 (2 H, d, J=8.5 Hz), 7.87 (1 H, dd, J=8.7, 1.7), 7.48 (2 H, d, J=8.1 Hz), 2.36 (3 H, s); MS m/e 325 (M+H)+. Anal. calcd. for C17H12N2O3S: C, 62.95; H, 3.72; N, 8.63. Found: C, 62.94; H, 3.68; N, 8.62.
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 24h;
3-formyl-lH-indole-5-carbonitrile, 1 g (1 eq, 5.9 mmol) was added to 50 mL round bottom flask, along with 1.63 g of potassium carbonate (2 eq, 11.8 mmol), dissolved in 30 mL of DMF. Mixture stirred at 80C. 0.81 mL of iodomethane (2.2 eq, 12.98 mmol) was added into the flask, let stirred for 24 hours. Residual solvent evaporated. Product crystallized with ethyl acetate, then filtered out. yield 99%. H NMR (500 MHz, DMSO-ife) delta 9.98 (s, 2H), 8.52 - 8.46 (m, 4H), 7.83 (d, / = 8.5 Hz, 2H), 7.74 (dd, / = 8.5, 1.6 Hz, 2H), 3.96 (s, 6H).
92%
With sodium hydride; In tetrahydrofuran; at 0℃; for 1.75h;
3-Formyl-1-methyl-lH-indole-5-carbonitrile lH-indole-5-carbonitrile (5.9 mmol, 1008 mg) was dissolved in 25 mL of THF and the solution was cooled to 0 C under N2-athmosphere. Sodium hydride (10.4 mmol, 250 mg) was added carefully in portions and iodomethane (9.6 mmol, 1368 mg) was added. The mixture was stirred at 0 C for 1 h. More iodomethane (4.8 mmol, 684 mg) was added and the stirring continued for 45 min. The mixture was poured over ice and the resulting slurry was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and evaporated. This gave 1.0 g (92 %) of the title product. 'H NMR (500 MHz, MeOH-d4) 8 9.94 (s, 1H), 8.55 (s, 1H), 8.26 (s, 1H), 7.71 (d, 1H), 7.65 (d, 1H), 3.98 (s, 3H)
With trichlorophosphate; In N-methyl-acetamide; water;
Preparation 35 3-Formyl-1 H -indole-5-carbonitrile Phosphoryl chloride (4.24ml, 45.48mmol) was added dropwise to dimethylformamide (3.52ml, 45.48mmol) and stirred for 30mins at room temperature. A solution of 1H-indole-5-carbonitrile (5.39g, 37.9mmol) in dimethylformamide (10ml) was added dropwise. A solid precipitated, further dimethylformamide (10ml) was added to aid stirring and the reaction mixture was then stirred at room temperature for 3hr. Water was added to quench the reaction mixture which was then stirred for 18hr. The stirring was stopped and the reaction mixture was left to stand, after 24hr a pink solid had precipitated in the organic layer. The layers were separated and organic layer filtered, washed with water and dried to give the desired product (5.44g, 84%). 1H NMR (DMSO)delta 7.60-7.80 (m, 2H), 8.20-8.30 (m, 2H), 10.00 (s, 1H), 12.20-12.35 (s, br, 1H).
84%
In N-methyl-acetamide; water;
Preparation 35 3-Formyl-1H-indole-5-carbonitrile Phophoyl chloride (4.24 ml, 45.48 mmol) was added dropwise to dimethylformamide (3.52 ml, 45.48 mmol) and stirred for 30 mins at room temperature. A solution of 1H-indole-5-carbonitrile (5.39 g, 37.9 mmol) in dimethylformamide (10 ml) was added dropwise. A solid precipitated, further dimethylformamide (10 ml) was added to aid stirring and the reaction mixture was then stirred at room temperature for 3 hr. Water was s added to quench the reaction mixture which was then stirred for 18 hr. The stirring was stopped and the reaction mixture was left to stand, after 24 hr a pink solid had precipitated in the organic layer. The layers were separated and organic layer filtered, washed with water and dried to give the desired product (5.44 g, 84%). 1H NMR (DMSO) delta 7.60-7.80 (m, 2H), 8.20-8.30 (m, 2H), 10.00 (s, 1H), 12.20-12.35 (s, br, 1H).
3-[2-(3.4-dichlorophenyl)-ethenyl]indole-5-carbonitrile[ No CAS ]
[ 17380-18-6 ]
bromo[(3,4-dichlorophenyl)methyl]triphenylphosphorane[ No CAS ]
[ 791-28-6 ]
Yield
Reaction Conditions
Operation in experiment
With MgCl2; In tetrahydrofuran; water; ethyl acetate;
14) Removal of triphenylphosphine oxide from 3-[2-(3.4-dichlorophenyl)-ethenyl]indole-5-carbonitrile reaction mixture using MgCl2 (2.2 eq) n-Butyllithium (2.5M solution in hexanes, 3.6 ml) was added to a stirred solution of (3,4-dichlorobenzyl)triphenylphosphonium bromide (4.4 g) in tetrahydrofuran (20 ml) at 0-5 C. under nitrogen and the mixture then stirred at ambient temperature for 30 minutes. 3-Formylindole-5-carbonitrile (1.0 g) was added in portions over 5 minutes. The resulting mixture was stirred for 25 minutes, diluted with tetrahydrofuran (10 ml) and then heated under reflux for 2.5 hours. water (20 ml) followed by ethyl acetate (25 ml) were added to the cooled mixture and the layers were separated. The ethyl acetate layer was washed with water (2*30 ml) and then brine (30 ml), then dried (MgSO4) and the solvent removed in vacuo to give a residue which was analyzed by NMR for triphenylphosphine oxide content.
With MgCl2; In tetrahydrofuran; water; ethyl acetate;
14) Removal of triphenylphosphine oxide from 3-[2-(3.4-dichlorophenyl)-ethenyl]indole-5-carbonitrile reaction mixture using MgCl2(2.2 eq) n-Butyllithium (2.5M solution in hexanes, 3.6 ml) was added to a stirred solution of (3,4-dichlorobenzyl)triphenylphosphonium bromide (4.4 g) in tetrahydrofuran (20 ml) at 0-5C under nitrogen and the mixture then stirred at ambient temperature for 30 minutes. 3-Formylindole-5-carbonitrile (1.0 g) was added in portions over 5 minutes. The resulting mixture was stirred for 25 minutes, diluted with tetrahydrofuran (10 ml) and then heated under reflux for 2.5 hours. water (20 ml) followed by ethyl acetate (25 ml) were added to the cooled mixture and the layers were separated. The ethyl acetate layer was washed with water (2 x 30 ml) and then brine (30 ml), then dried (MgSO4) and the solvent removed in vacuo to give a residue which was analyzed by NMR for triphenylphosphine oxide content.
N-[(3-Methyl-1H-indol-5-yl)methyl]-2-[6-methyl-3-([3-[(methylamino)methyl]phenethyl]amino)-2-oxo-1(2H)-pyrazinyl]acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
Preparation 36 (3-Methyl-1H-indol-5-yl)methylamine The title compound was prepared by a similar method to preparation 8 from <strong>[17380-18-6]3-formyl-1H-indole-5-carbonitrile</strong> (preparation 35) (5.44 g, 32 mmol) to give the desired product as a white solid (2.57 g, 50%). 1H NMR (CDCl3) delta 2.35 (s, 3H), 4.00 (s, 2H), 7.00 (s, 1H), 7.15 (d, 1H), 7.35 (d, 1H), 7.50 (s, 1H), 7.80-8.00 (s, br, 1H).
With N-benzyl-trimethylammonium hydroxide; In water; at 50℃; for 5h;Sealed tube;
General procedure: 4-Nitrobenzaldehyde (263 mg, 1.74 mmol), was added to a vigorously stirring solution of water (10 mL) and heated to 50 C. Once the aldehyde was seen to dissolve, 3,4-dichlorophenylacetonitrile (307 mg, 1.65 mmol) was slowly added resulting in the formation of a suspension and the reaction mixture was stirred for a further 10 min. After this time, 40% N,N,N-trimethyl(phenyl)methanammonium hydroxide, [PhCH2NMe3(OH)], in water (7 mL) was added drop-wise to the reaction mixture and once addition was complete, the reaction vessel was sealed and stirring was continued at 50 C for 5 h. a yellow solid (60%), m.p. >300 C; 1H NMR (DMSO-d6): delta 8.73 (s, 1H, CH=C), 8.51 (s, 1H, H-2'), 8.39 (s, 1H, H-2), 8.09 (s, 1H, H-4'), 7.71-7.63 (m, 3H, H-6', H-7', and H-5), 7.55 (dd, J = 8.4, 1.3 Hz, 1H, H-6); 13C NMR (DMSO-d6): delta 137.5, 135.1, 134.6, 132.0, 131.0, 130.4, 129.8, 127.1, 126.3, 125.5, 125.3, 124.9, 120.3, 118.9, 113.7, 111.1, 102.9, 101.7; IR (KBr) numax/cm-1: 3296 (NH), 2222 (CN), 2207 (CN), 1623 (C=C), 1473 (Ar), 809 (Ar-Cl); m/z (ESI M - H) 336; HRMS (ESI M - H): Calculated for C18H9Cl2N3; Exact Mass: 337.0174, found: 337.0223. Anal. C18H9Cl2N3 (C, H, N).
Preparation of Intermediate ABA suspension of Intermediate AA (4.2 g, 24.7 mmol) and ammonium acetate(4.18 g, 54.34 mmol) in nitromethane (263.0 mL) was stirred at 90 C for 2 hours. The reaction mixture was concentrated under reduced pressure. The crude product was washed with 25% ethyl acetate in petroleum ether (2 chi 20 mL) and dried to afford Intermediate AB (3.5 g, 68%) as yellow solid. NMR (DMSO-t¼): delta 10.84 (bs, 1H), 8.67 (s, 1H), 8.43-8.40 (m, 211), 8.23 (d, J= 13.66 Hz; 1H), 7.68 (d, J= 8.29 Hz; 1H), 7.61 (d, J = 8.78 Hz; 1H). Mass (M-H): 212.0.
With ammonium acetate; at 90℃; for 2h;
Example 25 3-(2-Nitrovinyl)-5-cyano-1H-indole Combine <strong>[17380-18-6]3-formyl-5-cyano-1H-indole</strong> (10.60 g, 63.32 mmol) and a solution of ammonium acetate (10.60 g) in nitromethane (660 ml). Heat to 90C. After 2 hours, cool to ambient temperature to give a precipitate. Collect the precipitate by filtration, wash with 1:1 MeOH/water (500 ml), and dry to give the title compound: mp 247-251C. MS (ACPI): m/e 214.0 (M+1).
General procedure: To a solution of an appropriate indole, azaindole or alternative heterocycles (1.0 eq) and di-ferf-butyl dicarbonate (1eq. to 2 eq., more in particular 1.2 eq) in acetonitrile was added DMAP (0.1 to 0.5 eq. more in particular 0.1 eq). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with a saturated sodium bicarbonate solution. The phases were separated. The aqueous phase was extracted with dichloromethane. The organic phases were combined, washed with a saturated ammonium chloride solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The BOC-protected compound was used in the next step without further purification.
General procedure: The mixture of indole aldehyde (1.0 equiv.) and (Carbethoxyethylidene)triphenylphosphorane (1.3 equiv.) was dissolved in CH2Cl2 or Toluene. The reaction solution was refluxed for 18 h and the excess solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using 0-40% EtOAc in Hexanes as eluant to give the desired products 4a-4j.
General procedure: A mixture of 1 (0.735 g, 5 mmol) and 2/4 (5 mmol) were added in succession insingle lots to the TBAA melt, and the reaction mixture was heated at 100 C andmaintained for 15-20 min. On completion of the reaction, as monitored by TLC,the reaction mixture was cooled to room temperature; ethanol was added to thereaction mixture and was refluxed for 5 min to extract the ionic liquid into ethanol.After cooling to room temperature, the separated product (3/5) was filtered off andwashed with ethanol (2-3 ml) to afford pure 3/5 as insoluble product. The ethanolwas evaporated to recover TBAA, which could be reused at least four times withoutloss of activity.
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