Name: 132-32-1|9-Ethyl-9H-carbazol-3-amine|95%
Brand: Ambeed
SKU: A945894
Price: 5.0 USD
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1
[ 132-32-1 ]
[ 118-75-2 ]
[ 80546-37-8 ]

Yield	Reaction Conditions	Operation in experiment
98.5%		General procedure: (1) To a reactor containing 3-amino-N-ethylcarbazole, 1000 kg of ethanol was added,Heated to 50 ~ 60 C and stirred for 30 ~ 40min, 3-amino-N-ethyl carbazole thoroughly dissolved,Then transferred to the condensation reactor, the solution containing the reduction of 200kg,Continue to join the recycled content of more than 95% recycled ethanol 3000kg,Sufficient solvent to make the reaction uniform;(2) adjust the temperature to 40 ~ 45 , and then open the kettle cover,Into the content of 98% sodium acetate (industrial grade) 148kg, feeding time controlled at 10 ~ 25min;(3) Then put in the content of 99% of chloranil 116kg, the reaction is exothermic reaction,And the material presents solid-liquid mixture, the temperature increases, the material will thicken thick,Therefore, the feeding process to adjust the reactor jacket cooling water flow, and control the feed rate,To ensure that the temperature inside the reactor controlled at 40 ~ 45 , the reaction temperature is too high,And increase the stirring resistance, it will feed time control for 100 ~ 200min;(4) The addition is completed, and the temperature is maintained at 40-45 C for 3.5-4 h;(5) open the reactor jacket steam, temperature distillation ethanol,After the evaporated ethanol solvent is cooled and condensed by the heat exchanger which has already turned on the cooling water,Into the ethanol solvent tank, ethanol solvent can be applied directly.Steaming out the feeding amount of 65-75% ethanol solvent, and then adding ethanol solvent dosage of 40-50% water, and then open the reactor cooling water out of the valve, the cooling material to 40 ~ 45 ,Condenser cooling water inlet temperature control 7 ~ 10 ;(6) Open the bottom of the autoclave valve, open the transfer pump, the condensate into the filter press, washed,It is necessary to recover the ethanol solvent from the pre-water, if the ethanol content of the pre-water detection is less than 1%Then stop collecting.(7) filter press cake to continue washing until the filtrate colorless,Washed and pressed to make permanent purple RL condensate wet material;(8) Into the drying room vacuum drying, vacuum degree -0.05 ~ -0.07 Mpa,When the temperature reaches 68 ~ 75 , sample testing, water content control ? 0.3%Qualified to be out of the oven, have permanent solid purple RL condensate.The weight ratio of the materials is: 3-amino-N-ethyl carbazole: ethanol: chloranil: sodium acetate = 1: (18-22) :( 0.58-0.60) :( 0.72-0.75).
	With sodium acetate; In 1,2-dichloro-benzene; at 45 - 105℃;Product distribution / selectivity;	Example 5147 gm of 3-amino-N-ethylcarbazole in 1 lit of orthodichlorobenzene (ODCB) was charged in a reactor. The mixture was heated to 45 C and 122 gm chloranil and 105 gm of sodium acetate trihydrate were simultaneously added to the mixture over a period of 4 hrs. The resultant mixture was further heated to 105 C and the acetic acid generated was removed by distillation. The mixture was then further heated to 170C and a 0.35 gm catalyst mixture (containing equal quantities of Cobalt chloride and Manganese chloride) was added to the reacted mixture. Air was passed into the mixture for a period of 6 hrs at atmospheric pressure (lkg/cm2) till completion of reaction as monitored by TLC. The reaction mixture was cooled to 80C and filtered. The filter cake was washed with 250 ml of hot ODCB, and dried in vacuum at 100 C. The product was further purified. The yield was 185 g of the dioxazine compound (90% of theory). The high purity of the product is evident from the elemental analysis, IR absorption spectrum, mass spectrum, X-ray diffractogram, and from the performance properties.
	With triethylamine; In 1,2-dichloro-benzene; at 35 - 165℃; under 1500.15 Torr; for 7h;	In a 5000 ml reactor, 210 g of 3-amino-N-ethylcarbazole and 2000 ml of o-dichlorobenzene were charged and stirred to 35 C with stirring. 140.7 g of tetrachlorobenzoquinone was added and 105 g of triethylamine was added dropwise, (9-ethyl-3-carbazolylamino) -1,4-benzoquinone was added to the reaction mixture, and 1 g of copper sulfate was added to the reaction mixture to give a solution of 2,5-dichloro-3,6-bis (9-ethyl-3-carbazolylamino) 2g anthraquinone, shut off the reactor, through the oxygen, the pressure control at 0.2MPa, heating to 165 , maintaining this temperature for 4 hours, the end of the reaction, cooling to 100 discharge, filtration, followed by o-dichlorobenzene, Methanol and water were washed, dried to obtain 279.5 g permanent purple pigment crude product, the yield was 94.9%, content of 98.5%.

Reference： [1]Patent: CN106831537,2017,A .Location in patent: Paragraph 0018; 0019; 0020; 0021; 0022
[2]Journal of the Chemical Society of Pakistan,2016,vol. 38,p. 318 - 325
[3]Patent: US2026092,1929,
[4]Patent: WO2012/1708,2012,A1 .Location in patent: Page/Page column 12
[5]Patent: CN104031400,2016,B .Location in patent: Paragraph 0021; 0022

2
[ 86-20-4 ]
[ 132-32-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With palladium 10% on activated carbon; hydrazine hydrate; In tetrahydrofuran; methanol; ethanol; at 60℃; for 1.08333h;	General procedure: Pd/C (10%, w/w) (10 mg) was added to the solution of N-R-1-nitrocarbazole or N-R-3-nitrocarbazole (1 mmol, 1a-21a) in 15 ml methanol and 10 mL THF at room temperature. Then the mixture was heated to 60 C for 10 min. 2 ml of hydraziniumhydroxide in 5 ml ethanol was then added to the solution as dropwise for 5 min. The mixture was vigorously stirred at 60 C for 60 min and then the Pd/C was ltered off. Subsequent extraction with ethyl ether, distillation and recrystallization with ethanol and THF in vacuum gave white needle crystal (5b and 6b are liquid form). The crystal was dried in N2 flux for 10 min and placed in inertia atmosphere.
		c, 3- amino-N-ethyl carbazole 5g of N- ethyl carbazole and 50mL of methylene chloride was slowly added to a round bottom flask,Slowly placed under 8-13 2.5mL of concentrated nitric acid and stirred for 1h mounted, rotary evaporated dichloromethane, filtered, washed with water,Recrystallized from ethanol to give 3-nitro -N- they ethylcarbazole; 0.01g palladium on carbon was added to the solution of 3.6g of-N- Ethyl-3-nitro-carbazole200mL ethanol solution, followed by heating at reflux for 5-10 minutes,The 10mLWas dissolved in hydrazine hydrate25mL of ethanol was slowly added, the reaction mixture for 20-24 hours at 55-60 , filtration, rotary evaporation, recrystallization, vacuum drying yield
	With nickel; citric acid; In ethanol; at 45 - 55℃;	in the reactor was added 3-nitro-N-ethyl carbazole, ethanol,Nickel catalyst and citric acid promoter, the temperature was adjusted to 45 ~ 55 with constant stirring,The reaction 2.5 ~ 3.5h; after the reaction, the recovery of ethanol distillation,The nickel catalyst is filtered off to obtain 3-amino-N-ethylcarbazole.

Reference： [1]Australian Journal of Chemistry,2016,vol. 69,p. 1268 - 1276
[2]Journal of Organic Chemistry,2019
[3]Tetrahedron,2013,vol. 69,p. 8964 - 8973
[4]Advanced Synthesis and Catalysis,1996,vol. 338,p. 731 - 737
[5]Patent: DE266942,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 11,p. 475
[6]Advanced Synthesis and Catalysis,1996,vol. 338,p. 731 - 737
[7]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 1458 - 1461
[8]Patent: CN105294540,2016,A .Location in patent: Paragraph 0026
[9]Patent: CN106831537,2017,A .Location in patent: Paragraph 0017; 0018
[10]Inorganica Chimica Acta,2018,vol. 477,p. 206 - 211

3
[ 6318-43-0 ]
[ 132-32-1 ]
N-(9-ethyl-9H-carbazol-3-yl)-3-pyridin-4-yl-propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With dmap; 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide In N,N-dimethyl-formamide Heating;

Reference： [1]Block, Michael H.; Boyer, Scott; Brailsford, Wayne; Brittain, David R.; Carroll, Debra; Chapman, Steve; Clarke, David S.; Donald, Craig S.; Foote, Kevin M.; Godfrey, Linda; Ladner, Anthony; Marsham, Peter R.; Masters, David J.; Mee, Christine D.; O'Donovan, Michael R.; Pease, J. Elizabeth; Pickup, Adrian G.; Rayner, John W.; Roberts, Andrew; Schofield, Paul; Suleman, Abid; Turnbull, Andrew V. [Journal of Medicinal Chemistry, 2002, vol. 45, # 16, p. 3509 - 3523]

4
[ 6925-00-4 ]
[ 132-32-1 ]
quinoxaline-6-carboxylic acid (9-ethyl-9H-carbazol-3-yl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 815 - 820

5
[ 50668-21-8 ]
[ 132-32-1 ]
N,N,N-tris(9-ethylcarbazol-3-yl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 90℃; for 8h;Inert atmosphere;	Tris-(dibenzylideneacetone) di-palladium(0) (Pd2(dba) 3, 0.008 g, 0.04 mmol) and tri-tert-butylphosphine ((t-Bu) 3P, 0.034 g, 0.04 mmol) were dissolved under argon in 10 ml of dry toluene and stirred for 10 min at room temperature (preformation of the catalyst). Then the mixture of 3-amino-9-ethylcarbazole (0.56 g, 5.8 mmol), 3-iodo-9-ethylcarbazole (0.2 g, 1.0 mmol) and sodium tert-butoxide (0.56 g, 5.8 mmol) in 20 ml of dry toluene (30 ml) were added. The reaction mixture was heated at 90 C for 8 h. After cooling, the reaction mixture was diluted with ethyl acetate and the organic phase was washed with water and brine. After being dried over MgSO4 and filtered, the solvent was removed and the residue was purified twice by column chromatography using hexane/ethylacetate (5/1) as eluent. It was recrystallized from eluent. Yield of TCA (yellow amorfhous powder) 36%, (0.2 g). 1H NMR (300 MHz, DMSO-d6), delta (m. d.): 0.93 (t, 9H, J = 7.4 Hz, -CH3), 3.69-3.79 (m, 6H, -N-CH2), 7.27-7.36 (m, 4H, Ar), 7.41-7.58 (m, 10H, Ar), 7.78-7.95 (m, 7H, Ar). IR (KBr), (nu/cm-1): 3049 (C-H,Ar); 2979, 2931 (C-H,Aliph); 14805, 1468 (C=C,Ar); 1378, 1344, 1305 (C-N). MS(ACPI+, 20 V), m/z (%): 596 ([M + H]+, 100).

Reference： [1]Electrochimica Acta,2015,vol. 154,p. 119 - 127
[2]Monatshefte fur Chemie,2006,vol. 137,p. 1053 - 1062

6
[ 42466-67-1 ]
[ 132-32-1 ]
2-cyano-3-(9-ethyl-9H-carbazol-3-ylamino)-acrylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 186 - 191

7
[ 132-32-1 ]
[ 129460-09-9 ]
N₂-[(9H-fluoren-9-ylmethoxy)carbonyl]-N₄-(9-ethyl-9H-carbazol-3-yl)-L-asparagine-(1,1-dimethyl)ethyl ester [ No CAS ]

Reference： [1]Organic letters,2002,vol. 4,p. 4001 - 4004

8
[ 132-32-1 ]
[ 432505-55-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With dmap; ammonium hydroxide; 1,2-dichloro-ethane; triethylamine; In methanol; dichloromethane;	Example 9 4-Dimethylamino-N-(9-ethyl-9H-carbazol-3-yl)-butyramide To a solution of 3-amino-9-ethylcarbazole (500 mg, 2.38 mol), 3-(dimethylamino)butyric add (438 mg, 2.62 mmol, 1.1 equiv), triethylamine (0.398 mL, 289 mg, 2.85 mmol, 1.2 equiv) and DMAP (145 mg, 0.5 equiv) in CH2Cl2 (10 mL) was added EDC (500 mg, 2.62 mmol). The resultant solution was maintained at room temperature for 19 hours, and then poured into water and extracted with CH2Cl2 (225 ml). The combined organics were washed with water (125 ml), dried over anhydrous Na2SO4 and concentrated. Purification of the residue by flash column chromatography 10% MeOH/CH2Cl2 grading to 2% ammonium hydroxide/10% MeOH/CH2Cl2) provided 4-dimethylamino-N-(9-ethyl-9H-carbazol-3-yl)-butyramide (595 mg, 77%) as a tan foam.

Reference： [1]Patent: US6399631,2002,B1

9
C₇H₁₅NO₄S [ No CAS ]
[ 132-32-1 ]
C₂₁H₂₇N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 15h;	To a solution of carboxylic acid 2 209mg (1.00mmol), 3-amino-N-ethyl carbazole 3 210mg(1.00mmol) and 1-hydroxybenzotriazole 163mg(1.21mmol) in N,N-dimethylformamide 5ml, was added 1-ethyl 3-(3-dimethylamino) carbodiimide hydrochloride 231mg (1.21mmol). The mixture was stirred at room temperature for 15 hours. Water was added to the reaction solution and the crystal deposited was filtrated and washed with water and dried. The crude crystal obtained was purified with column chromatography (SiO2 10g, CHCl3 / MeOH = 50) and crystallized with diethyl ether to give 167mg of the compound of this invention Id-2 (the yield is 42%).

Reference： [1]Patent: EP1760073,2007,A1 .Location in patent: Page/Page column 8-9

10
[ 16051-87-9 ]
[ 132-32-1 ]
[ 1051372-57-6 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 5019 - 5034

11
[ 132-32-1 ]
[ 625-36-5 ]
[ 893725-95-6 ]

Yield	Reaction Conditions	Operation in experiment
95%		White powder, mp. 170-172 C; yield, 95%. A solution of AEC (210 mg, 1 mmol) in 10 mL THF and K2CO3(138 mg, 1 mmol) was stirred for 30 min at 0 C. Then 0.1 mL 3-chloropropanoyl chloride (0.1 mL, 1 mmol) was added to this mixture, stirred for 10 min and until TLC indicated completion of reaction with rapid stirred for 2 h at room temperature. The solvent was removed under reduced pressure and the raw product washed with water and petroleum ether. It was recrystallized from acetone.

Reference： [1]Journal of Biomolecular Structure and Dynamics,2020
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 5019 - 5034

12
[ 132-32-1 ]
[ 13421-00-6 ]
[ 1185288-09-8 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 6050 - 6056

13
[ 132-32-1 ]
[ 19230-50-3 ]
[ 1185288-11-2 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 6050 - 6056

14
[ 132-32-1 ]
[ 66950-63-8 ]
[ 436800-48-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium t-butanolate;bis(1,5-cyclooctadiene)nickel (0); 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; In 1,4-dioxane; at 80℃; for 3h;Inert atmosphere;	Representative Procedure (coupling of phenylsulfamate 3, Table 1, entry 1) is used as an example). SI-3. A 20-mL reaction vial was charged with Ni(cod)2 (6.8 mg, 0.025 mmol, 5 mol%>), SIPr»HCl (21.2 mg, 0.05 mmol, 10 mol%>), anhydrous powdered NaOtBu (67.2 mg, 0.7 mmol, 1.4 equiv), and a magnetic stir bar, all in a glove box. Subsequently, a solution of sulfamate substrate 3 (100.5 mg, 0.50 mmol, 1 equiv) and morpholine (52.4 mu, 0.60 mmol, 1.2 equiv) in dioxane (2.5 mL) was added. The vessel was removed from the glove box, and then heated to 80 C for 3 h. After cooling the reaction vessel to 23 C and concentrating under reduced pressure, the crude residue was loaded onto a silica gel column (2.5 x 10 cm) and purified by flash chromatography (9: 1 Hexanes: Ethyl acetate) to yield aminated product SI-5 (78.1 mg, 95% yield) as a white solid. R/ 0.29 (9: 1 Hexanes :EtO Ac). Spectral data match those previously reported (Barker et al, J. Am. Chem. Soc. 2009, 131, 15598-15599). Any modifications of the conditions shown in this representative procedure are specified in the following schemes, which depict all of the results shown in Tables 1 and 2.; SI-35 (Table 2, entry 8). Purification by flash chromatography (300: 150: 1 Hexanes:CH2Cl2:Et3N) afforded aminated product SI-35 (92% yield) as a white solid. Rf 0.30 (2: 1 Hexanes:CH2Cl2). 1HNMR (500 MHz, C6D6): delta 7.94 (d, J = 6.7, 1H), 7.74 (d, J = 1.7, 1H), 7.39 (t, J = 7.6, 1H), 7.21-7.16 (m, 4H), 7.07 (d, J = 8.2, 1H), 6.95 (d, J = 8.5, 1H), 6.91 (d, J = 8.4, 2H), 6.82, (td, J = 7.4, 0.8, 1H), 5.15 (s, 1H), 3.69 (q, J = 7.2, 2H), 0.92 (t, J = 7.3, 3H); 13CNMR (125 MHz, C6D6): delta 146.9, 140.8, 137.0, 134.9, 129.7, 128.3, 128.3, 128.2, 128.1 , 127.9, 126.0, 124.2, 123.3, 121.9, 121.0, 1 19.4, 1 19.1 , 1 15.6, 1 14.4, 109.2, 108.8, 37.4, 13.6; IR (film): 3383, 3048, 2974, 1598, 1504, 1489, 1470, 1299, 1229, 1 150 cm"1; HRMS-ESI (m/z) [M + H]+ calcd for C20Hi8N2, 287.1548; found 287.1551.

Reference： [1]Organic Letters,2012,vol. 14,p. 4182 - 4185
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 2171 - 2173
[3]Patent: WO2012/94622,2012,A2 .Location in patent: Page/Page column 22-23; 29

15
[ 98-01-1 ]
[ 132-32-1 ]
[ 922-67-8 ]
[ 109-77-3 ]
[ 1350619-94-1 ]