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[ CAS No. 731810-08-5 ] {[proInfo.proName]}

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Chemical Structure| 731810-08-5
Chemical Structure| 731810-08-5
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Product Details of [ 731810-08-5 ]

CAS No. :731810-08-5 MDL No. :MFCD09258897
Formula : C10H11ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 226.66 Pubchem ID :-
Synonyms :

Safety of [ 731810-08-5 ]

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Application In Synthesis of [ 731810-08-5 ]

* 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.

  • Downstream synthetic route of [ 731810-08-5 ]

[ 731810-08-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 731810-07-4 ]
  • [ 731810-08-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(2,2-dimethoxy-ethyl)-3,5-dinitro-benzoic acid methyl ester With ammonium formate In tetrahydrofuran; methanol; water at 35 - 45℃; for 0.666667h; Stage #2: With hydrogenchloride In methanol; water at 32 - 35℃; for 3h; 1 Preparation of 6-amino-1/-/-indole-4-carboxylic acid methyl ester hydrochloride compound 4: A 2-L Erlenmeyer flask was charged with 10% Pd/C wet catalyst (8.6 g), methanol (800 ml) and THF (160 ml). Ammonium formate (139.1 g, 2.21 mol) was then added with stirring and the mixture was heated to 35 0C. Water (100 ml) was added. Compound 3 was then added in small portions over 10 minutes. The reaction temperature was maintained between 40 0C and 45 0C by controlling the addition rate of 3 and proper cooling. The reaction mixture was stirred for 30 minutes after addition is complete. HPLC analysis indicated that the reaction was complete. The reaction mixture was cooled to room temperature. The catalyst was filtered off through a Celite pad and the Celite pad was washed with MeOH (50 ml). The filtrate was concentrated to remove volatile components under reduced pressure. EtOAc (500 ml) and water (75 ml) were then added and the mixture was stirred for 5 minutes. Organic phase was separated and the aqueous phase was extracted with EtOAc (200 ml). The combined organic solution was concentrated to dryness to afford light-yellow oil (79.17 g). MeOH (100 ml) was added to the oil intermediate. The resulting solution was then added to the solution of concentrated aqueous HCI (37 wt%, 82.8 g) in MeOH (600 ml) while the temperature was maintained at 32 0C. The reaction mixture was stirred for 3 hours at 35 0C. Solid product precipitated out during this period. HPLC analysis indicated that the reaction was complete. The reaction mixture was cooled to room temperature. EtOAc (500 ml) was added and the resulting mixture was stirred for 30 minutes. The solid was collect by filtration to afford 45.07 g of product. The filtrate was concentrated to afford a paste (331 g). EtOAc (400 ml) was added to the paste and the mixture was stirred for 30 minutes. The solid was then collect by filtration to afford the 2nd crop of product 4 (16.28 g). ). 1H NMR (300 MHz, DMSO-d6) δ 3.93(s, 3H), 6.97(d, 1 H, J= 1.8 Hz), 7.65(m, 1 H), 7.72(d, 1 H, J= 1.8 Hz), 7.80(s, 1 H), 11.81 (s, br, 1 H).
  • 2
  • (E)-methyl 2-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoate [ No CAS ]
  • [ 731810-08-5 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: (E)-methyl 2-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoate With hydrogen In methanol; water; ethyl acetate at 0℃; for 2h; Stage #2: With hydrogenchloride In water; ethyl acetate at 10℃; for 1h; 1 Preparation of 6-amino-1H-indole-4-carboxylic acid methyl ester hydrochloride 4 via direct hydrogenation of 2-(2-Dimethylamino-vinyl)-3,5-dinitro-benzoic acid methyl ester compound 2: Methanol (27 kg) and 2-(2,2-dimethoxy-vinyl)-3,5-dinitrobenzoic acid methyl ester 2 (10 kg, 33.87 mol) were charged into a reactor through the charge port. 10 % Palladium on Carbon Catalyst (0.4 kg) was then charged to the reactor as a slurry in water (2.5 +/- 0.5 Kg). Ethyl Acetate (123 +/- 3 kg) was added followed by addition of hydrogen portion wise. The internal temperature was maintained at approximately 00C through cooling and controlling the rate of hydrogen addition. After pressure was constant for more than 30 min, hydrogen pressure was kept at 50-60 psi and the temperature was maintained at 00C for 2 hours. The catalyst was filtered off through an inline filter (Note: Catalyst is pyrrophoric. Do not allow the catalyst to pull dry.) The filtrate was concentrated to remove approximately 95 % of the solvent volume by vacuum distillation at an internal temperature of less than 35 0C. Ethyl acetate (130L ) was added with stirring. 37% HCI (10kg) was then added slowly below 10°C. The resulting mixture was stirred at 10°C for 1 hour. The solids was filtered onto a plate filter and washed with methyl t-butyl ether (15L). The product (wet cake) was transferred to a vacuum dryer and dried at 23 +/- 3 0C to afford 4.6 kg of product 4 (60% yield).
  • 3
  • [ 952238-94-7 ]
  • [ 731810-08-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In 1,4-dioxane; methanol at 20℃; for 1h; 2.5 Step 5. Preparation OF 6-AMINO-1H-INDOLE-4-CARBOXYLIC acid methyl ester hydrochloride 2 (b) Intermediate 2 (c) (20 g, 63.6 MMOL) was dissolved in anhydrous ethyl acetate (350 mL) and 10% palladium on carbon (7.4 g, 6.36 MMOL) was added under argon. The mixture was hydrogenated at 1 atm until the reaction was judged complete by LCMS. The Pd catalyst was removed by filtering through diatomaceous earth, and the filtrate was reduced in vacuo. The crude 3,5- DIAMINO-2- (2, 2-DIMETHOXY-ETHYL)-BENZOIC acid methyl ester was dissolved in anhydrous methanol (40 ML), and 4.0 M HCI in dioxane (160 mL) was added. The mixture was stirred at ambient temperature for one hour. The precipitated solid was collected by filtration and washed with CH2CI2 and diethyl ether and dried under vacuum to produce Intermediate 2 (b) (hydrochloride) (11.85 g) as a gray solid. The filtrate was concentrated and more Intermediate 2 (b) hydrochloride (1.48 g) was precipitated. The combined yield for both batches of Intermediate 2 (b) (13.33 g) was 92%
  • 4
  • [ 731810-08-5 ]
  • [ 24424-99-5 ]
  • [ 731810-56-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In tetrahydrofuran at 20℃; for 3h; 122.1 First Step [Show Image] 6-aminoindole-4-methyl carboxylate hydrochloride (1.5 g, 6.62 mmol) was added to a mixed solution of a THF solution (20 mL) and an aqueous 4 N sodium hydroxide solution (4 mL). To the reaction solution, di-tert-butyl dicarbonate (1.73 g, 7.92 mmol) was added, followed by stirring at room temperature for 3 hours. The organic layer was separated and washed with an aqueous saturated ammonium chloride solution (2 mL), and then the solvent was distilled off under reduced pressure. The resulting residue was washed with a mixed solution (1:20) of THF and heptane and then collected by filtration to obtain 1.83 g of methyl 6-(tert-butoxycarbonylamino)-1H-indole-4-carboxylate. 1H-NMR (400 MHz, DMSO-d6) d (ppm): 1.49 (s, 9H), 3.87 (s, 3H), 6.82 (s, 1H), 7.40 (s, 1H), 7.8-7.9 (m, 2H), 9.40 (br, 1H), 11.25 (s, 1H); ESI-MS (m/z): 291 [M+H]+.
  • 5
  • [ 731810-08-5 ]
  • [ 1169790-06-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-amino-1H-indole-4-carboxylic acid methyl ester hydrochloride With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 5℃; for 2h; Stage #2: With water; ammonium chloride In tetrahydrofuran Cooling with ice; 91.1 First Step [Show Image] To a THF solution (15 mL) of 6-aminoindole-4-methyl carboxylate hydrochloride (0.9 g, 4.66 mmol), lithium aluminum hydride (300 mg, 7.89 mmol) was added while cooling to 0°C, followed by stirring at 0 to 5°C for 2 hours. An aqueous saturated ammonium chloride solution (1.5 mL) was gradually added to reaction mixture under ice cooling and the solvent was distilled off under reduced pressure. To the resulting residue, water (15 mL) was added, followed by extraction with ethyl acetate. The resulting organic layer was washed with a saturated brine solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 110 mg of (6-amino-1H-indol-4-yl)methanol. 1H-NMR (400 MHz, DMSO-d6) d (ppm): 4.8-5.0 (m, 2H), 6.23 (s, 1H), 6.43 (s, 2H), 6.7-6.8 (m, 1H), 6.92 (s, 1H), 7.15 (d, 1H, J = 6.6 Hz), 10.40 (s, 1H).
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