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[ CAS No. 29906-67-0 ]

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Chemical Structure| 29906-67-0
Chemical Structure| 29906-67-0
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Product Details of [ 29906-67-0 ]

CAS No. :29906-67-0MDL No. :MFCD07772841
Formula : C9H8N2O2 Boiling Point : 339.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :176.17Pubchem ID :147322
Synonyms :

Computed Properties of [ 29906-67-0 ]

TPSA : 50.8 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.11 Rotatable Bond Count : 0

Safety of [ 29906-67-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 29906-67-0 ]

  • Upstream synthesis route of [ 29906-67-0 ]
  • Downstream synthetic route of [ 29906-67-0 ]

[ 29906-67-0 ] Synthesis Path-Upstream   1~12

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YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; 10percent Pd/C (0.18 g/g of startingmaterial) was added to a solution of starting material dissolved inTHF (54 mL/g of starting material). Reaction flask was sealed andvacuum was used to remove air. A balloon filled with hydrogen gaswas then attached to the flask. The reaction was stirred at roomtemperature for 24e48 h or until disappearance of starting materialwas observed by TLC. The reaction was then filtered through celite.Filtrate was rotovapped to give a brown solid; 100percent; 1H NMR(DMSO): δ 7.15-7.05 (m, 2H), 6.71 (dd, J 3.0, 0.9 Hz, 1H), 6.57 (dd,J 8.5, 2.1 Hz, 1H), 6.12 (dd, J 3.0, 0.9 Hz, 1H), 3.67 (s, 3H); 13CNMR (DMSO): δ141.30, 131.12, 129.49, 129.44, 129.41, 112.31, 110.11,104.21, 99.13, 32.86.
95.8% With iron; acetic acid In ethanol at 78℃; for 1 h; 1-Methyl-5-nitro -1H- indole (270mg, 1mmol), Fe powder (1.12g, 20mmol, 10equiv) was added ethanol (15ml) and glacial acetic acid (2ml) in, 78 heated at reflux for 1h, TLC monitoring. After completion of the reaction, it was filtered through Celite, washed with ethanol to precipitate a colorless, ethanol rotary evaporation. The solid was dissolved in ethyl acetate followed by the addition, ultrasonic minutes, extracted with saturated NaHCO3 wash, water, NaCl wash, saturated MgSO4 dry. The organic layer by rotary evaporation, dried, the crude product was purified by column chromatography to give 230mg of yellow product, 1-methyl-5-amino-1H- indole, yield 95.8percent.
95.5% With palladium on activated charcoal; hydrogen In ethanol at 50℃; for 5 h; A2 (1.0 g, 5.7 mmol) was dissolved in ethanol and catalyzed with Pd/C and H2 for 5 hours at 50°C. The catalyst was filtered off and the solvent was removed to give 0.85 g of A3. The yield in this step was 95.5percent without further purification.
81% With hydrazine hydrate In ethanol at 80℃; for 1 h; Inert atmosphere General procedure: Hydrazine hydrate was chosen as the hydrogen donor for the low emission of pollutants. In a typical procedure, hydrazine hydrate (4 equiv) was added into the reactor which containing fresh prepared catalyst as described above. Then the reactor was put into a preheated oil bath with a stirring speed of 500 rpm, and the substrate (1 mmol)dissolved in 1 mL ethanol was added drop-wisely under argon. The reactions were monitored by TLC. After the reaction, the reaction mixture was vacuum filtered through a pad of silica on a glass-fritted funnel and an additional 15 mL of ethyl acetate (5 mL portions) was used to rinse the product from the silica, the filtrate was concentrated in vacuum and analyzed by GC. Products were purified by column chromatography and identified by 1H NMR and 13C NMR.
77% With hydrogen In tetrahydrofuran; ethanol for 4 h; Step G: Synthesis of 1 -methyl- lH-indol-5 -amine as an intermediate <n="38"/>; [0100] A mixture of l-methyl-5-nitro-lH-indole (2.00 g, 11.3 mmol) and platinum (IV) oxide (0.20 g, 10percent by weight) in a mixture of ethanol (20 mL) and tetrahydrofuran (20 mL) was shaken under an atmosphere of hydrogen at 40 psi for 4 h. After this time, the mixture was filtered through diatomaceous earth and concentrated under reduced pressure. Purification by flash chromatography (silica, 1 :3, ethyl acetate/hexanes) afforded 1-methyl- lH-indol-5-amine (1.28g, 77percent) as a red oil: 1H NMR (500 MHz, CDCl3) δ 7.12 (d, J= 8.5 Hz, IH), 6.95 (d, J= 3.0 Hz, IH), 6.92 (d, J= 2.0 Hz, IH), 6.69 (dd, J= 2.0, 8.5 Hz, IH), 6.28 (d, J= 3.0 Hz, IH), 3.72 (s, 3H), 3.47 (bs, 2H).
27% With tin(ll) chloride In ethyl acetate at 20℃; To l-methyl-5-nitro-lH-indole (0.5g, 2.84mmol) in ethyl acetate (10ml), tin (II) chloride hydrate (2.5g, 11.4mmol, 4eq) was added and the reaction mixture stirred overnight at room temperature. The reaction mixture was basified with aqueous sodium EPO <DP n="50"/>hydroxide solution (pH 8) and the compound extracted using ethyl acetate. The crude compound obtained was purified by column chromatography over silica gel using ethyl acetate/ hexane (1:1) as eluent to give 1 -methyl- lH-indol-5ylamine (120mg, 27percent).

Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 1202 - 1213
[2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 10, p. 3531 - 3541
[3] New Journal of Chemistry, 2015, vol. 39, # 7, p. 5360 - 5365
[4] Patent: CN104163815, 2017, B, . Location in patent: Paragraph 0065; 0066; 0068
[5] Patent: CN107163029, 2017, A, . Location in patent: Paragraph 0049; 0053; 0054; 0055; 0056; 0057; 0058
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1461 - 1464
[7] Catalysis Communications, 2016, vol. 84, p. 25 - 29
[8] Patent: WO2009/42907, 2009, A1, . Location in patent: Page/Page column 36-37
[9] Synthetic Communications, 1998, vol. 28, # 1, p. 147 - 157
[10] Canadian Journal of Chemistry, 2003, vol. 81, # 10, p. 1108 - 1118
[11] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 48-49
[12] Journal of Medicinal Chemistry, 1993, vol. 36, # 8, p. 1104 - 1107
[13] Organic Letters, 2004, vol. 6, # 17, p. 2897 - 2900
[14] Archiv der Pharmazie, 2005, vol. 338, # 2-3, p. 67 - 73
[15] Journal of the American Chemical Society, 2005, vol. 127, # 22, p. 8050 - 8057
[16] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5509 - 5513
[17] Patent: WO2006/40520, 2006, A1, . Location in patent: Page/Page column 125-126
[18] Patent: US2011/190299, 2011, A1, . Location in patent: Page/Page column 22-23
[19] Synthetic Communications, 2013, vol. 43, # 4, p. 498 - 504
[20] Patent: CN106349241, 2017, A, . Location in patent: Paragraph 0571; 0572; 0573; 0574
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Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 10, p. 1108 - 1118
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Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 10, p. 1108 - 1118
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Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 10, p. 1108 - 1118
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1 h;
Stage #2: at 20℃;
Step F: Synthesis of l-methyl-5-nitro-lH-indole as an intermediate; [0099] To a mixture of 5-nitro-lH-indole (5.0 g, 30.8 mmol) in λ/,λf-dimethylformamide (100.0 mL) was added sodium hydride (60percent in mineral oil, 1.35 g, 33.9 mmol), and the mixture stirred for 1 h at room temperature. After this time, iodomethane (2.11 mL, 33.9 mmol) was added, and the mixture was stirred at room temperature overnight. After this time, saturated aqueous ammonium chloride (100 mL) was added and the organics extracted with ethyl acetate (150 mL). The organics were then washed with 5percent aqueous lithium chloride (200 mL), water (200 mL) and brine (1000 mL), dried over magnesium sulfate and concentrated under reduced pressure to afford l-methyl-5-nitro-lH-indole (5.42 g, 100percent) as an orange/brown solid: 1H NMR (500 MHz, CDCl3) δ 8.59 (d, J= 2.0 Hz, IH), 8.13 (dd, J = 2.0, 9.0 Hz, IH), 7.34 (d, J= 9.0 Hz, IH), 7.20 (d, J= 3.0 Hz, IH), 6.67 (dd, J= 0.5, 1.0, 3.0, 3.5 Hz, IH), 3.86 (s, 3H).
100%
Stage #1: With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1 h;
Stage #2: at 20℃;
Dissolve A1 (10.0 g, 61.7 mmol) in 100 ml of N,N-dimethylformamide.A tetrahydrofuran suspension of NaH (2.7 g, 112.5 mmol) was slowly added dropwise and reacted for 1 hour at room temperature. 4.3 ml of methyl iodide was added and the reaction was stirred overnight at room temperature. After the reaction was completed, it was washed with 1 L of saturated ammonium chloride solution and extracted with 500 ml of ethyl acetate to obtain an organic layer. Then, 400 ml of a 5percent lithium chloride solution, 1 L of water, and 1 L of brine are successively washed, and the organic layer is added with anhydrous magnesium sulfate. After drying overnight, the solvent was removed to obtain 10.9 g of A2. The yield of this step was 100percent, which was completely converted into the target product.
92% With potassium hydroxide In acetone at 0℃; for 10 h; Heating / reflux To a solution of 5 -nitro-1 H-indole (2.Og, 12.3mmol) in acetone (20ml), powdered potassium hydroxide (3.4g, 60.7mmol, 5eq) was added followed by the addition methyl iodide (2.6 Ig, 18.5mmol, 1.5eq) at O0C. The reaction mixture was heated to reflux for 10 hr. The solvent was evaporated and water was added. The compound was extracted with ethyl acetate, dried over anhydrous sodium sulphate, filtered and the organic layer was concentrated to dryness to yield l-methyl-5 -nitro-1 H-indole (2.Og, 92percent). The crude compound was used in the next stage without purification.
47.5% With potassium carbonate In acetonitrile at 80℃; The 5-nitroindole (972mg, 6mmol), K2CO3 (1.66g, 7.2mmol) was dissolved in acetonitrile (20ml), a 80 °C was heated at reflux for several hours, until TLC monitored the reaction. After rotary evaporation and then, solid was dissolved in ethyl acetate, added saturated NH 4Cl solution and extracted. The organic layers were combined, spin crude done. Finally, the product was purified by column to give the intermediate 1-methyl-5-nitro-indole -1H- 769mg. Yield 47.5percent.

Reference: [1] Patent: WO2009/42907, 2009, A1, . Location in patent: Page/Page column 36
[2] Patent: CN107163029, 2017, A, . Location in patent: Paragraph 0049; 0050; 0051; 0052
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5509 - 5513
[4] Synthetic Communications, 1998, vol. 28, # 1, p. 147 - 157
[5] Organic Letters, 2004, vol. 6, # 17, p. 2897 - 2900
[6] Journal of the American Chemical Society, 2005, vol. 127, # 22, p. 8050 - 8057
[7] Patent: WO2006/123145, 2006, A1, . Location in patent: Page/Page column 48
[8] Patent: WO2018/171575, 2018, A1, . Location in patent: Page/Page column 23; 33; 35; 67
[9] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 10, p. 3531 - 3541
[10] Collection of Czechoslovak Chemical Communications, 2006, vol. 71, # 5, p. 679 - 690
[11] Organic Letters, 2013, vol. 15, # 1, p. 112 - 115
[12] Chemistry - A European Journal, 2016, vol. 22, # 13, p. 4400 - 4404
[13] Patent: CN104163815, 2017, B, . Location in patent: Paragraph 0065-0067
[14] Journal of Organic Chemistry, 1986, vol. 51, # 19, p. 3694 - 3696
[15] Journal of Medicinal Chemistry, 1993, vol. 36, # 8, p. 1104 - 1107
[16] Journal of Medicinal Chemistry, 1992, vol. 35, # 1, p. 177 - 184
[17] Organic Letters, 2010, vol. 12, # 21, p. 4956 - 4959
[18] Patent: US2011/190299, 2011, A1, . Location in patent: Page/Page column 22-23
[19] Chemical Communications, 2014, vol. 50, # 81, p. 12181 - 12184
[20] Organic and Biomolecular Chemistry, 2017, vol. 15, # 28, p. 5904 - 5907
[21] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 1202 - 1213
[22] European Journal of Medicinal Chemistry, 2018, vol. 160, p. 120 - 132
[23] Patent: US6242470, 2001, B1,
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YieldReaction ConditionsOperation in experiment
97.1% With potassium carbonate In n-heptane; ethyl acetate; N,N-dimethyl-formamide Example 14
Synthesis of 1-methyl-5-nitroindole.
A 500 mL, three-necked flask equipped with a thermocouple, condenser, and addition funnel was charged with 5-nitroindole (20.0 g, 12.3 mmol), potassium carbonate (4.0 g, 29 mmol), N,N-dimethylformamide (80 mL) and dimethyl carbonate (22 mL, 26.14 mmol).
The resulting mixture was heated to reflux.
The reaction was monitored by HPLC or TLC (solvent system: 30percent ethyl acetate in heptane).
An analysis of the reaction mixture after 3 h at reflux, by the above methods, failed to detect any remaining 5-nitroindole.
The reaction mixture was then cooled to 10+-5° C. and diluted with water (160 mL) which resulted in the formation of a yellow precipitate.
After the mixture was stirred at room temperature for 2 h, the solid was collected by filtration, then was washed with water (100 mL) and dried under high vacuum at 60-65° C. for 24 h to give 1-methyl-4-nitroindole (21.1 g, 97.1percent) as a yellow solid.
Reference: [1] Patent: US6326501, 2001, B1,
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Reference: [1] Organic Process Research and Development, 2009, vol. 13, # 1, p. 67 - 72
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 13, p. 5758 - 5764
[3] Patent: US2009/149662, 2009, A1, . Location in patent: Page/Page column 8-9
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Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 6, p. 604 - 608
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 5, p. 1461 - 1464
[3] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 1954 - 1957
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Reference: [1] Patent: WO2006/40520, 2006, A1, . Location in patent: Page/Page column 124-125
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Reference: [1] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000427
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Reference: [1] Organic Process Research and Development, 2009, vol. 13, # 1, p. 67 - 72
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Reference: [1] Synthetic Communications, 2013, vol. 43, # 4, p. 498 - 504
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